Come Fly With Me
by angel-castiel-rules-the-world
Summary: Castiel is an ex-USAF fighter pilot who teaches people to fly. He lives in the sky and cares little for anything else. Gabriel has to deal with his brother's public relation disasters. Dean in a mechanic who has never stepped foot on a plane in his life and is extremely happy to continue this status quo for the rest of it. Sam has other plans for his brother. Destiel. Human AU.
1. Chapter 1

**Hello lovely people. So this idea came to me and wouldn't let go. I was planning on waiting to start it for a while and finish off some of my other stories. But, I didn't so here you are. I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel Novak had wanted only one thing in his life. He wanted to fly. And so at the tender age of 18 he joined the United States Air Force where they paid for him to study at university so he could become a fighter pilot. Which he succeeded in doing, gaining the call sign Angel. He in fact became one of the best there was, with his natural ability to feel at one with whatever aircraft they placed him in. Everyone said he would go far, or well they did until he opened his mouth. See while Castiel could fly like no other, he was rather socially awkward (and by socially awkward I mean he said whatever he was thinking and screw the consequences). As such he only made it to major before he was forced to retire from flying and become an instructor. Oh he could and would still fly, he just couldn't do the dog fighting. He only lasted a year of training the new generation before he could hack it no more. He hated having to sit on the side-lines while the people he trained went and risked their lives for his country. And so it was with that that Angel hung up his wings. Or at least the Air Force ones.

So Castiel returned home only to be confronted by his brother looking for his latest project. See Gabriel Novak collected companies and businesses like most people collected dvd's (not that Castiel knew this). He had a whole portfolio of them and as of yet not one of them had ever failed (though whether that was down to him or the shit hot teams he employed to run them was debatable). So anyway Gabriel claimed he was looking for something to do, and Castiel was the perfect solution to his boredom. And so was born Heavenly Wings Flight Training Company.

And of course the true reason for Gabriel's involvement was not because he knew his brother would refuse to take a cent from him, even if he did tell him that he was a millionaire (honest). So instead Gabriel created work for his brother that involved flying and thus making Castiel's world better. What he hadn't taken account of, of course, was that his brother would not be just flying the planes, he would be training the people too. Which meant he would have to communicate with them. Which might not have been the best idea he had ever had.

* * *

Dean Winchester also only wanted one thing in his life, and that was for his little brother Sam to be happy. They'd had a pretty crappy childhood with their mother dying when Sam was still a baby and their father having to travel around the country for work before dying when they were young too. They spent most of their time with their 'Uncle' Bobby, who was in fact their fathers best friend and had taken them in in an attempt to give them some sort of stable home life. It was there that Dean learnt to work on cars. And he was amazing at it. By the age of 14 he was in Bobby's scrap yard fixing up all the broken cars he could find. Once fixed he and Bobby sold them, Dean keeping the profits and saving them. It was with these savings that he managed at the age 25 buy his own auto-body shop. Dean never went to college, no that was Sammy's thing. But he could fix anything you asked him too.

He was proud of his little brother. He had become a great lawyer and returned to their home town to practice, bringing with him his college girlfriend who was now his fiancée and soon to be his wife. And this is the point our story begins, because as much as Dean loved Jess and thought she was great for his brother he did not agree with all her ideas. Namely the one in which said that getting married on the beach in Hawaii would be soooo romantic. Because Dean Winchester did not fly. Ever. Period. Not going to happen.


	2. Chapter 2

**Hello again my darlings. I would like to thank those of you who have followed and favoured this story since I published it. You're awesome. So here we are with the next chapter of my new story. I hope you like it.**

 **Oh yes, the bits in italics are memories.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel pulled up outside the hanger of the small airfield he worked out off with a sigh. He hated having to teach idiots to fly, but he had to earn a living somehow. And at least this way he got to be up there too. With that thought his mind went back to his heydays as a fighter pilot. Going up against the best of the best and winning, but that wasn't now. He had been out of the Air Force for 11 months, 2 weeks and 6 days. Not that he was counting. No if anyone was doing that it was his brother with whom he had decided (stupidly) to go into business with after leaving the air force. Still it paid the rent on his small one bed flat. And as previously stated, he got to fly.

Castiel was interrupted from his musing by said brother banging on his window.

"You coming Cassie? Cos your late." Gabriel shouted to him though he knew it would gather only one response from him. And yep there it was, the eye roll. Sometimes Gabriel wondered why he was doing this to himself. He and Castiel had been in business together for the last six months, with Castiel teaching people to fly and Gabriel managing everything else. Though to be honest Gabriel was surprised they had any clients left, what with Cassie treating them like his cadets or trainees or whatever they called them at that flight academy thingy (it was all so very Top Gun in his opinion). Anyway he really didn't want to piss off the customers they still had. So Castiel better get his ass out of the car and over to the hanger pronto or Gabriel might just resign. Again. Well in all honesty for the 8th time, in the last month. (See this is what happens when he had to do all the work himself.)

Castiel really wanted to be able to tell his brother to stick it, but he knew he couldn't. If he wanted to be able to fly, he needed a plane. And to buy a plane he needed money, and for that he needed to teach people to fly. But damn they really were all complete idiots. And rich idiots at that who knew nothing but there pampered lives. God he hated the rich (though that could be more because he wasn't one of them than anything else).

* * *

Dean Winchester sat in his car with his hands gripping the steering wheel so hard they were turning white. Damn his little brother, if he could he would seriously consider killing him, or at least beating him up. But he knew he couldn't because he knew he was right. He just didn't like admitting it. Why did Sam and Jess have to go get married in bloody Hawaii anyway? What was wrong with one of the 48 states on the mainland USA that he could drive to? Why did they have to choose the one of the two states which required flying to get there? With that thought Dean closed his eyes and remembered the conversation he and Sam had had last week.

* * *

 _Dean was happily at his auto-body shop minding his own business servicing a customer's Ford humming to himself as he worked._

 _"Dean I know you're scared of flying-" Came his brother's voice behind him making him stand up quickly and whack his head on the bonnet of the car. Son of a bitch._

 _"What? No I'm not Sam." he replied emphatically rubbing the back of his head, damn he was likely to have a bruise there tomorrow._

 _"Yeah right. Anyway I thought that maybe if you had some flying lessons that would help." Sam continued as if Dean hadn't really said anything of any importance._

 _"No need." Dean glared at him and crossed his arms leaning back against the car. They had had this conversation many times since Jess and Sam had announced where they were getting married and Sam just kept suggesting he learnt to fly. Though how in the hell that would help, Dean had no freakin' idea._

 _"Well I've actually already booked and paid for them so you kinda have to go." Sam replied handing Dean a fait accompli while also holding out some papers to him, which Dean being Dean refused to take._

 _"What?" he asked instead, surely Sam hadn't really gone and done that right?_

 _"Flying lessons with Heavenly Wings Flight Training Company. No idea what there like there new just know that the instructor is one Major Castiel Novak. Formerly of the US Air Force. So he should know what he's doing right?" Sam replied checking the papers in his hand to make sure he got the information right._

 _"Hmm." Was all Dean could say to that._

 _"Look Dean you have to go. You're my best man, I can't exactly get married without you there can I?" Sam asked with a begging expression on his face that usually worked on his brother._

 _"Why you getting married in Hawaii anyway?" Dean grumbled refusing to look at Sam._

 _"We've been over this Dean. It's what Jess wants." Sam replied the begging tone even going in to his voice now._

 _"Fine. But I don't need no lessons." Dean tried one last time to argue, though they both knew he was losing._

 _"You're going Dean, please for me?" and with that Sam Winchester brought out his secret weapon of the puppy dog eyes that his brother just could not say no to._

 _"Fine." Dean growled and turned away._

* * *

The Dean in the present opened his eyes hoping against hope that he would find himself anywhere but the parking lot of the air field, though the hope was in vain. He hadn't miraculously been transported anywhere else. Nope he was still here, trying to build the courage to go and have his first ever flying lesson. God damn it.


	3. Chapter 3

**Why hello again my dears. So next bit. Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

"Well look at that. The 'client' isn't here. I can't really teach someone to fly if they don't show up now can I?" Castiel smirked as he entered the office adjacent to the hanger using finger quotes on the word client.

"I'm sure they will show. Mr Winchester was most instant." Gabriel replied only half concentrating on the conversation as he checked over the books in front of him, not even looking up as Castiel entered.

"You mean he's a pushy assbutt." Castiel responded folding his arms as he leant against the desk next to his brother and tried to read what Gabriel was working on.

"No. and really? Assbutt?" Gabriel asked finally looking up at his younger brother. I mean who says that?

"Yeah assbutt. Just like you." Castiel replied accompanying the comment with a smile while bumping his hip against his big brothers shoulder.

"Go get the plane ready, I'll deal with Mr Winchester when he arrives." Gabriel said with a sigh knowing full well that Castiel would annoy him no end until he let him get into the air.

"Fine. But if he's not here in five minutes I'm taking off without him." Castiel replied with a new spring in his step at the thought of getting off the ground for the first time that day.

"That kinda defeats the purpose of teaching someone to fly if there not with you doesn't it?" Gabe asked under his breath. Luckily Castiel didn't hear him or he would have no doubt given him another mouth full. Damn he didn't know how the air force had put up with him for the last 15 years. He'd only been working with him for six months and he was getting ready to strangle his own brother. And Gabriel bet that this Mr Winchester had turned up, listened for like a second to Cassie's ravings and just left again. His brother really needed to learn some people skills if this business was going to stay afloat. (Without Gabriel having to bribe people to come and learn to fly that is. Though it was getting precariously close to that situation.)

* * *

Dean walked slowly towards the office door then stopped and turned round taking a step back towards the parking lot.

"No you can do this. For Sam." He muttered under his breath and turning again to walk towards the door. Once there he just stood and stared for what felt like forever before, with a mutter of Sam's name, he reached out and grabbed the handle and pulled the door open.

Once inside Dean found himself in a sparsely furnished office, it had three chairs and a desk and that was it. well not quite, one of the chairs was occupied with a blonde guy who Dean thought was probably a few years older than him who had, was that gold eyes? Who had gold eyes? Well this guy obviously. It was at that point that Dean realised he was staring and he hadn't actually said a word upon entering, wow way to give the wrong impression Dean. Blushing bright red at this realisation he muttered.

"Hi I'm Dean Winchester, my brother booked me lessons."

Gabriel was busy with paper work when the door went. Looking up he guessed that it would be Mr Winchester but the person standing in front of him looked nothing like he had imagined from the phone. This guy was rugged, and was that oil on his fingers? And why was he just staring at him? Did he like what he saw? That thought made him chuckle, though in truth the guy was hot, with his short dirty blonde hair and piercing green eyes, or at least he was if you were that way inclined at any rate, which Gabriel was not. Cassie on the other hand… Oh now this could be interesting.

Gabriel sat there just watching the guy wondering what he would do when he suddenly turned bright red and mumbled something.

"I'm sorry I did quite catch that." He said to the guy with his professional smile on his face.

"I'm Dean Winchester. My brother booked me some lessons." The man said louder this time. Well at least that explained why he didn't look like the self-assured businessman Gabriel had been expecting. That man was his brother.

"Very well Mr Winchester. I have some forms I need you to fill out and I'll just go get your instructor." With that Gabriel handed Dean a clipboard filled with forms and went out to the hanger to round up Castiel. He **really** wanted to be present for the first meeting between these two.

* * *

Castiel was busy doing his pre-flight checks when Gabriel came up to him with the biggest smirk, on his face. In fact his brother looked decidedly like he had just won the lottery or something. Which as you can imagine instantly made Castiel go on high alert. That was a look you never trusted on Gabriel's face.

"Mr Winchester's here." Gabriel announced making Castiel look round him but he couldn't see anyone else.

"Where?" he asked. What was his brother up to now? Normally Gabriel kept the clients as far away from him as possible until it was too late for them to back out. And that was the way they all preferred it.

"In the office filling out the paper work." Gabriel replied nonchalantly.

"Why are you telling me this?" Castiel snapped at him. What was going on?

"Oh I just really think you should come in and met him, is all." Gabriel replied now looking smug more than anything else, before he turned and walked back the way he came.

Castiel was in two minds, on the one hand he didn't want to follow Gabriel on principle cos he really didn't trust his brother, but on the other he really wanted to know just what was going on. With a sigh he gave in and followed Gabriel back to the office only to come face to face with the most gorgeous green eyes he had ever seen. Running his eyes discreetly up and down the body which was attached to them he realised that the rest of the man really wasn't too shabby either.

Dean had stood as Gabriel came back in and handed over the forms, Gabriel directed him to the door to the hanger and he was just about to go through when it opened and there standing in front of him was the most beautiful man he had ever seen. He had the bluest eyes, and the messiest black hair and an air of some indefinable quality about him. It was obvious that he was used to being in command, and that the military stance was ingrained in him. So this must be Major Novak, the man who had the joy-est job of teaching him to fly. Oh crap… Dean suddenly realised he had a massive teenage crush on his teacher. How much more embarrassing could you get? At that thought he blushed once again and turned back to Gabriel who was trying really hard not to rub his hands together in joy at the anticipated fun he could have with these two who obviously had the hot's for each other whether they knew it or not.

Oh yes this was going to be So. Much. Fun.


	4. Chapter 4

**Well hello my darlings. I must say I was amazed at the response this story got. I woke to 20 emails the other morning. I would like to make a special thanks to** **lovely21 and rainystv for the great reviews. I would also like to thank all you love people who have followed and favoured since my last update.**

 **So here we are, next chapter I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel watched the client, Mr Winchester, turn from him with blush and look back at Gabriel which made his eyebrows raise. Now why would this rather interesting human specimen be interested in his extremely straight brother? Surely his gaydar wasn't that off. Because the fact that this guy was gay screamed at him as loudly as F-16's doing a fly by. Oh well it was of no consequence to him, though if Mr Winchester did try to chat up Gabriel he would be happy to sit back and watch. If nothing else it would give him some entertainment in what would no doubt be a boring ass day once he came back to the ground.

Gabriel saw Mr Winchester blush again and smirked. He really was wondering just what was going through the guys' head that he kept blushing like that. But be that as it may it seemed Castiel wasn't going to do the introductions so he probably should.

"Mr Winchester, this is Major Castiel Novak-" Gabriel started only to be interrupted by his brother who had taken up lounging against the doorframe to the hanger.

"Retired." Castiel said with a sigh. How many times did he have to remind his brother of that?

Gabriel just rolled his eyes. As if he didn't know Cassie was retired before he continued. "Retired Major Castiel Novak and he will be your flight instructor. Castiel this is Mr Winchester." He finally got out.

"Dean, call me Dean." Dean said looking briefly at his instructor before looking back at Gabriel. If he wasn't careful he would start staring into those blue eyes and never look away. Looking at the other guy was much safer in his mind.

"Very well Dean. Shall we go?" Castiel asked straightening up. He was getting a bit fed up with watching the guy, Dean, eye his brother when he could be in the air. Couldn't he do that once the lesson was over?

"Umm, don't you have to, I don't know, go through safety stuff or something first?" Dean squeaked out. Surely they wouldn't be flying in the first lesson right? Right?

"Are you scared Dean?" Castiel asked in his low voice as he stepped into the other man's personal space and caught his eyes with his own. Showing him just how to eye another man.

"What no of course not." Dean bristled. He wasn't about to let these guys know that in actual fact he was bricking it at the thought of leaving the ground.

"because if you were I'm sure myself or Gabriel could find a way to ease your" at that point Castiel paused running his eyes once again over Dean's body before he lowered his voice even more and continued. "Mind."

At that Dean just made choking sounds, he couldn't speak, let alone think. Just what the hell had he walked in on here? What had his brother got him involved with? What the hell was going on?

"Cassie behave." Gabriel said as he decided that enough was enough and gently pushed his brother back from their client and glaring at him before turning to Dean who seemed to be on the verge of hyperventilating, though whether at the thought of flying or because of Cassie's behaviour Gabriel didn't know. The fact that this guy was afraid to fly of course came through loud and clear to him. "Sorry about my brother Dean-o, he's a dick but he is also the best pilot the air force ever had. You'll be fine." He said in his most soothing voice capturing the other man's eyes reassuringly.

"Not worried." Dean strangled out looking into the gold eyes. He still couldn't get over them. They were not normal.

"Good, then let's go shall we?" Came a growled voice and with that Castiel turned as if he was on the parade ground and marched back to the hanger. Dean turned to Gabriel with a look of helplessness on his face that Gabriel had seen so many times when people first met Castiel. And as such instead of speaking he just made shooing motions with his hands until Dean reluctantly followed the retired (and he was pretty sure crazy) Major.

Once they were gone Gabriel let himself chuckle. Well that certainly was entertaining, he had never seen his brother get jealous of him before. Hmm, maybe he should play that up a bit. You know, just to get both their heads out of there asses and their lips connected to each other's. with that thought he settled back down at his desk to go over the books once more hoping he could find some money from somewhere in them.

Dean followed the Major to a small two-seater plane but there he baulked. They were going up in that? It barely looked like it would hold them on the ground it was so flimsy.

Castiel turned to Dean to tell him to get inside when he caught his look of horror at his Angel. Now people could say what they liked about him, he didn't give a shit. But insult his wings and then they would have a problem. As such he narrowed his eyes at Dean and crossed his arms.

"Do you have a problem with the plane Mr Winchester?" He asked slowly pronouncing every word perfectly.

"You mean apart from the fact that a) you're flying it and b) that it looks like a freakin' tin can?" Dean responded crossing his arms as well and glaring right back at the extremely hot-when-angry pilot. "Not at all." He finished with but too late the damage was done.

"You can leave now." Castiel growled at him, clenching his fists and keeping his arms crossed so he didn't take a swing at the guy.

"Gladly." Dean spat out though he didn't move. Just who the hell did this guy think he was?

"Good and don't come back until you learn some respect." Castiel snapped out.

"Respect? For what? This piece of trash?" Dean asked waving his hand dismissively at the plane. Castiel just glared. That was it. This man had gone too far.


	5. Chapter 5

**Hello again. Well here we are the next chapter I hope you likey.**

 **Disclaimer: I don't own Supernatural.**

* * *

Gabriel was sitting at the desk working away when he heard the plane take off. Thank god, it had taken longer than normal for Castiel and the client to leave but they finally had. Or at least that was what he thought until the door to the office from the hanger slammed open and Dean stormed in covered in what looked like dust and muck from the hanger floor. Oh god what had his brother done now?

"Your brother is a righteous ass." Dean snapped at him throwing himself down in a chair. He needed to rant at someone so this guy would do.

"I know. What did he do this time?" Gabriel asked resigned to them losing yet another client, though he had to hand it to his brother, this was the first time he had lost one before he even got them into the plane.

"He tried to freakin' run me over with his freakin' plane that's what he did." Dean screeched at him making Gabriel's eyebrows raise. That was a bit extreme even for Castiel.

"Why?" he asked realising he was probably only getting one side of the story here.

"Something about me not showing his tin can respect." Dean grumbled.

"Please tell me you didn't call his plane a tin can to his face." Gabriel muttered, oh please god no. what did he do to deserves this?

"And so what if I did?" Dean asked defensively. It was a tin can.

"If you did Dean Winchester then you are rather lucky to be alive." Gabriel said with exasperation at not just the man in front of him but his brother as well.

"What the hell is his problem anyway?" Dean asked I mean what was it with that guy?

"Are you telling me you don't have something you love so much that if someone insulted it you would happily kill them?" Gabriel asked finally snapping, he might be able to slag of his brother but this man could not.

Dean thought about that for a moment before he realised what Gabriel was saying. Yeah okay, now he felt a bit like an ass, but he was not going to admit that to either of the Novak's. "That's different." He mumbled when he looked up and found Gabriel still glaring at him.

"How?" Gabriel asked though he thought that Dean would say something like because they were a person or something. Therefore his response startled Gabriel so much he barked out a laugh.

"Because baby is my car." Dean replied defensively.

"Oh my god you too are made for each other." He finally got out being chuckles. I mean Cassie had his plane and Dean-o had his car.

"What do you mean?" Dean asked suddenly going on alert with this guy.

"As special friends?" Gabriel replied with a smirk on his face as he watched Dean narrow his eyes at him.

"I don't know what you're talking about." He said dangerously low not that Gabriel was bothered. He could take Dean easily.

"I'm talking about the fact that you fancy the pants off of my little brother. And that he feels the same way." Gabriel replied with a shrug and leaning back in his chair to watch Dean's reaction. Hmm he wondered if this guy was even out. Well whatever Dean's response to his statement should answer that question.

"No he doesn't." Dean mumbled when he realised that there was no point denying his attraction to Castiel to his brother. It seemed that this man's gold eyes saw everything damn it.

Ah there it was. "Got ya." Gabriel said with a smirk making Dean's eyes widen. The damn man had been playing him.

"You can't tell him." He said defensively. It was one thing for him to know, quite another for the focus of his attraction to be made aware.

"Oh don't worry, I'm not going to. I'll leave it to him to work out." Gabriel replied with a wave of his hand. It would be fun to see just how long it would take Cassie to realise that it was him that Dean was having wet dreams about rather than Gabriel himself.

"No way. I mean he's not interested." Dean replied dismissively, why would a guy like Castiel be interested in him? Then there was the fact that of course Castiel was also straight.

"Are you saying you know my brother better than I do?" Gabriel asked in disbelief. Was this guy blind?

"No, but he was in the military." Dean said though even to him the words sounded stupid.

"You ever heard of don't ask don't tell Dean-o? please." Gabriel replied with a roll of his eyes. I mean really?

"oh." Was all Dean said. Hmm, maybe Castiel wasn't as straight as he thought he was. Not that that changed the fact that there was no way he would be interested in him.

"Yeah oh. Now would you like to book your next lesson with us at Heavenly Wings Flight Training company? We give the best of experiences." Gabriel asked with his professional smile on his lips and a pen in his hand hovering over the extremely empty appointment book.


	6. Chapter 6

**Hello again my dears. Here we are another chapter, enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel stayed out for as long as he could and even when he landed his angel he took an inordinate amount of time cleaning her down so she would be ready for his next flight. He knew that when he did go back to the office Gabriel would chew him out for losing them yet another client. And yes okay, he may have over reacted when he flew off leaving Dean to dive out of the way of the wings. But he was pissed, hell he still was pissed. He hoped that jumped up prick had left and wasn't still hanging round the office trying to flirt with Gabriel.

Finally having done everything he possibly could to put it off, he returned to the office. Walking through the door the first thing he noticed was that Gabriel was alone thank god. With that thought he threw himself into the chair opposite his brother ready to be lectured at.

"Bit extreme trying to run him over don't you think?" Gabriel said not looking up from the paper work his was going through. Once he had finished the page he was working on he put his pen down and did look up at his brother then. "You could have dented angel." He said in a humorous voice.

"What, that's it?" Castiel asked in disbelief. Where was the ranting and the disappointed looks.

"Yes. Considering Dean-o has booked another lesson despite that, yes I think that just about covers it." Gabriel replied leaning back in his chair watching his brother.

"Yeah well he probably only did that so he could see you again." Castiel grumbled not sure how he felt knowing that he would be seeing Dean again. Gabriel would probably make him apologise or something.

"Ah yes. The staring. He is extremely attractive don't you think? Hmm maybe I should ask him out for a drink, what do ya reckon?" Gabriel asked trying really hard to keep a straight face at the flash of annoyance that crossed his brother's face at his words.

"You're straight Gabriel." Castiel replied evenly. He had no idea what his brother was up to now.

"There's an exception to every rule Castiel." Gabriel said with complete sincerity on his face, even if he was lying out of his ass. He was a damn good actor when needed.

"And you have a girlfriend." Castiel continued as if Gabriel hadn't spoken.

At that Gabriel chuckled. Yes he did have a long term girlfriend, not that Castiel had ever met her. Hmm, maybe he could - at that his eyes twinkled as he turned to his brother again.

Castiel was watching Gabriel chuckle and crossed his arms he didn't see what was so funny about this. But it was when Gabriel turned to him with twinkling eyes he knew he was in deep shit.

"And how do you know that Cassie?" Gabriel asked smirking at him.

"You told me." Castiel stated with narrow eyes. Just what was his brother getting at now?

"But how do you know I wasn't lying? I could be as free and single as you." Gabriel said with a wave of his hand. He wasn't but he could be.

"Even if you were you're still straight." Castiel argued back though he didn't know why he was bothering, what was it to him what his brother did? Or who he did for that matter?

"Hmm, maybe Dean-o could change my mind?" Gabriel said contemplatively. He found it so hard not to burst out laughing at his brothers glowering face, he wondered if Castiel really was as dense as he was pretending to be. Surely he was aware that he was attracted to Dean-o.

"Do whatever you want I'm not going to stop you, but piece of advice don't date someone just to piss off you brother. Not that it would piss me off." Castiel replied gruffly. It wouldn't piss him off if Gabriel dated Dean, not really. Yeah okay it might get a bit annoying to watch them around the office and - but it didn't matter, it was all academic anyway, Gabriel was straight.

"Liar. Your pissed that he likes me more than you." Gabriel responded smirking at Castiel. Wow this really was fun.

"No I'm not. Why would I care about who Dean Winchester likes?" Was Castiel's snarky response to that.

"That's the question isn't?" and with that Gabriel went back to his paper work while Castiel sat there frowning trying to work out just what the hell Gabriel was trying to get at. And what the hell was going on in his own mind. Which let's be honest wasn't something he spent much time doing. Personal reflection was not one of his strong points.

* * *

Sam went round to the Winchester auto-body shop that afternoon on the surface to go see how his brother was doing, though in truth he went to see if 1. His brother had actually gone to his flying lesson and 2. How it had gone.

"Hey Dean." He shouted as he entered the garage but couldn't see his brother.

"Over here." Came a shout from underneath some red car. Sam wasn't very good at knowing what was what when it came to motors. As long as they got him from A to B he didn't really care much.

Walking over he arrived just as Dean pushed himself out.

"Hey what's up?" Dean asked Sam casually as he got up. Oh he was pretty sure he knew exactly why his brother was here. But he would make him work for it before he told him how his stupid idea could have got him killed. Without even leaving the ground.

"I came to see if you went to your lesson this morning." Sam replied he was not going to beat around the bush, they both knew why he was here.

"I went." Was all Dean responded.

"And? Come on Dean what happened?" Sam asked. His brother was behaving rather oddly, well even more oddly than normal that is.

"Well let's see, I made a complete idiot of myself, I insulted the instructor's plane and he then tried to run me over with said plane." Dean answered counting the things off on his hand. He didn't mention that fact that he had a massive crush on said instructor. There were just some things Sammy did not need to know.

"What the hell Dean?" Sam asked completely thrown by Dean's list. Just what in the name of heaven had Dean done now?

"Hey don't go blaming me they are freakin' crazy man." Dean defended himself with. And they were, well at least Castiel was definitely certifiable.

"So I take it you're not going again." Sam's response was resigned. He had tried and failed. Damn it, he needed to make sure he could get Dean in a plane before his wedding.

"Well I might have booked another lesson for next week." Dean mumbled as he quickly turned around and walked away to his office not looking Sam in the eyes. It wasn't his fault that he was going again, the golden eyed guy could be kinda persuasive.

"Really? You are voluntarily going back in a plane?" Sam asked following him. What was he missing here?

"Well I kinda never got as far as getting into the plane this morning." Dean replied turning to look at him with a frown as if he had only just realised that fact for himself.

"Okay just, just start from the beginning." Sam said he couldn't take this story in dibbles and unconnected sentences anymore. He needed Dean to lay it out for him.

And so Dean did. He explained about his meeting with Castiel and yes he may have waxed a little too lyrically about the guy's gorgeous black hair and beautiful blue eyes, and that deep, gravelly voice. And yes okay the only thing he might have said about the other guy (whose name he didn't actually know he realised) was that he had gold eyes, but it meant nothing, not to Dean.

To Sam on the other hand it told him all he needed to know. His brother had the hots for his flight instructor and that was the one and only reason Dean was going back again. Well Sam would take any advantage he could if it got Dean into a plane. He just hoped that this Castiel didn't hurt his emotionally constipated brother in the process.


	7. Chapter 7

**Hello my dears. I would like to thank rainystv and lovely21 for the wonderful reviews. I would also like to thank those of you who have followed and favoured since my last update.**

 **So here we are, the next chapter, I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Dean sat at his desk doing his least favourite thing. Paperwork. He was going through the invoices from a new supplier he had started using when something on the paper caught his eye. It was the name of the owner of the company. One Gabriel Novak. Hmm, Novak, can't be that common a name and so, more because he really didn't want to do the paperwork and anything would be preferable and as such it would be a great form of procrastination, he googled the name. What came up surprised him somewhat (and by somewhat I mean had he been standing he would have had to sit down, as it was he nearly fell of his chair). Because when he googled that name pictures came with the information that the man was a multimillionaire with a list of companies as long as his arm, and those pictures were of the golden eyed man from the flight place. What the hell? If he was this guy then why on earth was he running the flight company? I mean surely he could afford someone else to do that. And some more furniture Dean added as he remembered the spartan office.

Reading on, cos now he was actually interested in what was going on at that place, he discovered that Gabriel had a really hot long term girlfriend who ran her own multimillion dollar business and that he was currently on a sabbatical. Hmm, why take a sabbatical to start up a shitty little flight company with his brother? Well it looked like Dean would have a lot of questions for this Gabriel at his next lesson.

* * *

Gabriel was sitting at his desk spining in his chair as he thought. He loved his brother, he really did, and he wanted him to be happy. But Castiel had gone from high school straight to the air force and flying and had as such never (to Gabriel's knowledge at least) had a relationship with anything other than his planes. And Gabriel felt it was a bout time that changed (and not just because Gabriel thought that if Castiel was in a happy relationship he might just be a bit nicer to their clients). He had, in the back of his mind, been trying to think of someone he could set Cassie up with for a while, but all attempts he had made had failed miserably as Castiel seemed to just sleep with the guys and then never contact them again. There was no way his brother could even consider having a relationship with someone if he wasn't going to give them time to get to know him. But now here was Dean-o. In Gabriel's mind he could well be just what Cassie needed, but how to make sure that Castiel actually got to know the guy, and had time to let actual feelings develop between the two of them? That was the question he was currently trying to find the answer to.

* * *

Dean walked through the door to the office of Heavenly Wings Flight Training Company wondering just why the hell he had agreed to come back here. I mean why did he book this damn lesson? Then of course there was the other question of why, when he realised that this was a seriously bad idea, he didn't just phone to cancel. Just what was his damn brain playing at now? But that was kinda beside the point now, what with him walking through the door and all.

"I'll be with you in a minute." Came the voice from under the desk that he recognised as Gabriel's, what he was doing under the desk was a mystery and as such Dean just had to walk up and find out.

"Hello Gabriel." He said to the man who was crouched on the floor.

At the sound of his voice Gabriel looked up holding a pen in his hands as he smiled up at one of their very few remaining clients. "Hello Dean-o. so you do know my name." He replied as he stood and moved to sit back in his chair gesturing for Dean to do the same on the other side of the desk.

"I know a lot more than that." Dean said smirking as he sat down.

"Really?" Gabriel asked with the raise of his eyebrow waiting for Dean to reveal just what he had discovered, and how.

"Oh yes. What I don't know is what a guy with your…assets is here, doing this." Dean said waving his hand around vaguely hoping Gabriel understood.

Which of course he did. Gabriel was nothing if not extremely quick thinking. Which explained his answer to Dean's not really asked question.

"Why are you here, doing this Dean-o? Cos we both know you hate flying." He asked linking his hands together and resting his chin on top of them.

"For my brother." Dean replied with a shrug. It was no secret he guessed.

"Ditto." Gabriel replied smiling and leaning froward on his desk.

"So now I know all your secrets." Dean said with a smirk as he copied Gabriel's position and also lent on the desk.

"Not all of them." Gabriel replied lowly, he had just heard the creak of the door as if it was opened a crack and he knew that Castiel was spying on him and Dean. What he didn't know was why, but it did give him an idea of how to get Cassie and Dean-o to become friends. And so with a twinkle in his eye and a sensual smile on his lips he moved his left hand so that his finger was gently stroking the back of Deans hand and with his right he scribbled something on a pad. All the time his eyes never left the eyes of the man opposite him.

Dean watched Gabriel move his finger to stroke his hand and his eyes went wide. What the actual hell? He would put money on the fact that this guy really did not swing that way, so why was he acting as if he was flirting with Dean? Before he could open his mouth and demand to know what Gabriel thought he was doing he also heard the creak from behind him and he realised that this conversation was less private than he thought it was. After a quick evaluation of the pros and cons he closed his mouth once more. If Castiel thought that he liked Gabriel then he would not realise that it was him that he liked and as such his secret would be safe. He really didn't want Castiel to know about his infatuation with the guy. I mean that would just make everything so god damn awkward.

"But I'll happily share some of them with you, maybe over a drink sometime?" Gabriel asked flirtatiously while simultaneously moving the pad so the Dean could read what he had written and gesturing with his eyes for him to take a look.

Which of course Dean did. It was a simple message.

 _Follow my lead, trust me._

And so against his nature Dean did just that.

"Yeah that sounds good, tomorrow night work?" Dean managed to squeak out. Just what was he doing?

"Tomorrow will work brilliantly Dean-o." Gabriel replied with his best come to bed smile on his face. Damn he should get an Oscar for this performance.

Before Dean could reply there was a cough behind them making Dean jump and turn round while Gabriel just sat back and smirked at Castiel who was now leaning against the door frame glaring at Gabriel as if he could smite him with just a look.

"When you to have quite finished I believe Mr Winchester has a lesson with me." Castiel said his voice dripping sarcasm.

"Um yeah." Dean replied standing eye darting round the room, not settling on any one thing making him look extremely guilty. With that Castiel humped and turned and marched out of the office with Dean following meekly.

Once they had left Gabriel leaned back in his chair and put his feet up on his desk grinning manically. Castiel would have to get to know Dean-o now. And he wouldn't touch the guy if he thought that he was dating Gabriel. Yes, a goods days work so far, he just hoped that Dean wouldn't let the cat out of the bag once those two got into the air.


	8. Chapter 8

**Hello again. I would like to thank those of you who have followed an favoured since my last update. Here's the next chapter. Hope you likey.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel was in the hanger, waiting for Dean Winchester to come and have his second lesson. He was even in the mind to maybe apologize for trying to run him over, if he was polite this time that was of course. But he didn't arrive. Looking at the clock Castiel noticed it was a two minutes past 2, and Dean's lesson had started at two o'clock on the dot. Frowning Castiel made his way to the door to the office, about to demand that Gabriel locate his wayward pupil when he heard voices. Now normally Castiel would have just marched into the room no matter what. But something stopped him, maybe it was the conversation he and Gabriel had had the last time that Dean Winchester had been here. Had Gabriel been serious about his interest in Dean? Logically and academically Castiel would say the answer to that was a clear cut no. but... (and that was the reason he didn't march into that room, the but) but... what if his brother was telling the truth? What if Gabriel was interested in Dean? It wasn't like Castiel had kept track of his brothers relationships (or his anything for that matter) over the last 15 years. Maybe Gabriel did like men as well as women, how would he know? He of all people knew that what people said and what they thought where two very different things when it came to certain subjects. And so instead of storming in and demanding Dean join him this minute he slowly cracked the door open, cursing silently when it creaked, he just hoped those in the office didn't notice and he listened.

"So now I know all your secrets."

"Not all of them." He heard Gabriel reply clearly but in a low voice which made his eyes go wide.

His brother had secrets and Dean knew some of them. He needed to know what was going on in that room. With that he pushed the door open a little more so that he could see just what was going on in the office, though looking through the crack he had created he realised he didn't need to be as stealthy as he was being, the two men in the room only seemed to have eyes for each other. Typical. With that he pushed the door open completely and leaned against the door frame. What he heard almost made him fall down in shock. Gabriel asked Dean out. Gabriel, his brother whom he had always been pretty sure was straight, had just asked a guy out for a drink. What the fuck? At that he turned to Gabriel but instead of the dewy eyed look of someone who had just arranged a date with someone they really liked he caught a calculated look upon his brothers face, which was quickly exchanged for a smug one when Gabriel's eyes rose to Castiel's. Oh bloody hell, just what freaking game was Gabriel playing now? And was Dean aware of it? Cos the guy had seemed taken with Gabriel the last time. Not that it was any of his business what these two got up to. Gabriel could look after himself and he was sure the Dean could as well. It was not his problem, no his only problem right now was that they should be in the air rather than on the ground, with that he coughed to interrupt the two men and get Dean into the cockpit. He wanted, no needed to be in the air right **now**.

* * *

Castiel tried really hard to stay silent on the way to the plane but he found he couldn't.

"So you're dating my brother." He said gruffly to Dean whose head shot up. He had been in a world of his own trying to work out what had just happened in the office.

"Um, yeah it looks like that." Dean replied still not quite believing in himself. Just what was Gabriel up to?

"You do know he's straight right?" Castiel snarked at him getting his back up instantly. What was this guys problem anyway?

"Well obviously not that straight. I am most definitely all man." Dean smirked back, take that Castiel.

"Is that so?" Castiel replied turning to openly runing his eyes up and down Dean's body.

Dean saw Castiel eyes and knew there was two responses to that look, and he felt he had blushed enough to sink a small battle ship in front of this guy and as such went for the flirtatious response instead. And so taking a step closer to the other man he lowered his voice to reply.

"Oh yeah."

Castiel watched Dean move closer to him, he could feel the spark between them, which under any other circumstances Castiel would have taken full advantage of, but this guy had just agreed to go on a date with his brother. And now he was flirting with him, Just what was going on? With that he smiled up at Dean and leaned towards him as he said "Hmm, maybe I will have to find out the proof of that for myself, someday, when your not dating my straight brother."

With that Castiel turned back round and finished making his way to the plane. He was extremely confused about what was happening here. Little did he know he wasn't the only one. Dean was just as confused. Though he decided that Castiel was only flirting with him because he didn't think that he should be dating Gabriel. Maybe he didn't think he was good enough for his brother?

Dean followed Castiel and got into the plane pretty much on autopilot, it wasn't until he was strapped into the passenger seat that he suddenly remembered where he was and what he was about to do. This was not helped by Castiel speaking to him in a professional voice rather than the snarky sassy one he had got used to.

"Now how many times have you been in a plane?" Castiel asked as he flicked switches and settled his radio over his ear.

"None." Dean replied, his hands going to the side of the seat and grabbing hold for dear life as Castiel started the engine. They hadn't even moved yet and Dean just wanted to get out, now.

"Great," Castiel muttered under his breath before he continued loud enough for Dean to hear as he started taxing out of the hanger and towards the runway."Lets start at the beginning then. I'll fly this time I think don't you?"

"Okay." Dean barely managed to get out, his breathing was already coming fast as they sped up along the runway.

"Don't worry I promise not to go crazy. Wouldn't want to upset Gabriel." Castiel said turning to his passenger and taking perverse pleasure in the white face that greeted him as he pulled the plane into the air. Time to fly.

* * *

Dean couldn't breath, or he was going to be sick, he wasn't sure which but he was pretty sure that it was one of those two. He hated this, it was not natural. To be up so high, no don't think about it, just breath, breath. He refused to look out of the window, in fact he had closed his eyes. If he couldn't see that he was in the air then surely he could pretend he wasn't. Not that he was fooling himself at all but at least he could concentrate on his breathing and not puking all over the cockpit. Would sick in the dial things in front of him make the plane stop working? Would that make them crash? Oh god, oh god, he was going to die in a plane crash. Okay don't think about crashing. Its fine everything is fine. Your in baby going down a really smooth road, that's all, not flying and not in a plane.

* * *

Castiel took in the joy of being in the air, thankful that his passenger wasn't one for talking. He loved this, this freedom, and with Dean being silent he could pretend he wasn't there. After about five minutes of this silent commune with his angel he felt he should probably get on with some actual teaching. After all Dean wasn't paying him to just fly them around. Turning to address Dean, explain some things, he found himself confronted with a white face which had eyes screwed so tightly closed that it had to hurt. In fact Dean's mouth seemed to be just as closed. Oh hell, he better not be sick inside angel. With that thought he started running through what he had in the plane, suddenly remembering he had a paper bag behind his seat, moving so he could grab it he held it out to Dean, not that the other guy could see it.

"Here take this. If you throw up in angel I will kick you ass." he grunted, making Dean open his eyes a fraction and turn to the man next to him, though he didn't speak, he just grabbed the bag and put it over his mouth, using it to help his breathing while valiantly trying to keep the puke down.

"So guess your not a big flyer then." Castiel remarked as he watched Dean out of the corner of his eye as he flew the plane.

At that Dean just shook his head, though then he realised his mistake as the sick he had been keeping down suddenly came up with a vengeance, it was a good thing that he had the bag over his mouth already in his mind.

"Lovely." Castiel said sarcastically but Dean could swear he also heard amusement in the guys voice which made him glare at him as he dry heaved a few more times.

"you done now?" Castiel asked when it seemed the Dean had empted his stomach plus some into the bag, not that he expected a response from the man next to him. "So I'm turning us round and taking us back down, but it could take a few minutes so just relax okay? I'm not going to let anything happen. I'm good at this, your safe with me." he continued in a gentle voice, the kind you would use on a scared animal or child.

Though it seemed to work as Dean sat back into his chair, though Castiel wasn't sure if that was because he was more relaxed or if throwing up had taken everything out of him.

"So Dean, if you hate flying that much why you doing this?" He asked, he was confused. Surely there was no reason for Dean to put himself through this.

"Have to." Was the weak response he got from Dean. Which he had to say was an improvement, at least the guy was talking now.

"Okay, well we're on the final approach now, so not long til I have you back on solid ground." Castiel said with a reassuring smile to his passenger.

"Thanks Cas." Dean mumbled out, once again closing his eyes as the plane dipped down towards the ground. The knowledge that they were heading back to safety didn't stop his stomach churning at the descent and he really didn't think he had anything left to heave. He just wanted to get back to earth and never leave it ever again.


	9. Chapter 9

**Hello again, again. I would like to thank you lovely people who have favoured and followed since my last update.**

 **So here's the next chapter. I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

Once the plane was back on the ground and in the hanger Dean struggled to undo his seatbelt, somehow he had lost his hand eye co-ordination and as such it seemed stuck. Castiel who had gotten out and made his way round to Dean's side just shook his head as he opened the passenger door and leaned in to release him. Making Deans breathing go crazy again but this time for a whole other reason, rather than fear it was due to Castiel's proximity to him. Damn he really needed to get a hold of himself here.

Castiel took his time undoing Deans straps. He found he rather liked being up close and personal with the man. But no, that wasn't to be, he was dating Gabriel. Hmm, when Dean had left he and his brother where going to have a little talk about that. But that was for later. Right now he just needed to get Dean into the office.

With that in mind Castiel helped Dean out of the plane, and when it became clear that his legs wouldn't hold him up he slung Dean's arm over his shoulder and supported him to the door.

Once he had got it open he helped Dean into the room and placed him gently down on one of the chairs in front of Gabriel's desk and knelt down beside him, murmuring that everything was alright and rubbing Deans back as the man bent over and put his head in his hands.

"What's going on?" Gabriel asked. He had stood when he heard the plane return, though he hadn't gone to the hanger to see what had happened, he wasn't sure if he wanted to be confronted with what was no doubt to be a highly angry Castiel. But instead of Cassie storming in and landing him one as he expected he watched his brother carefully help Dean in and gently settle him down on a chair, all the while murmuring gentle and reassuring words to the guy. Well this was definitely something new, as such he really felt he should be clued in.

"Your boyfriends a little upset." Castiel responded snarkily at him. Ah yes there was the brother he knew and loved.

"What did you do Cassie?" He asked cautiously making his way round the desk so he could lean on it but not approaching the pair.

"Nothing I didn't even take him on a loop the loop or anything." Castiel defended, what did his brother think he had done?

"Its true, I just, I don't think I can do that again." Dean replied briefly raising his head so his eyes caught Gabriel's before he lowered it once more.

Gabriel was about to try to find a persuasive argument to keep Dean on their books when Castiel spoke. Though it was more the way he said the it than the words themselves.

"Why you doing this Dean?" Castiel asked gently to the man who was still completely white.

"Because my brother is getting married in freakin' Hawaii and I need to fly to get there." Dean replied sitting back in his chair and tipping his head back while keeping his eyes closed.

At his movement Castiel noticed just how close he was to the man who was supposedly dating his brother. With that he stood and took a step away so he was positioned at the same distance as Gabriel was from Dean, though he made the third point in the triangle (the irony of which was not lost on Gabriel, who lets be honesty was the only one who even understood it) before he spoke.

"So you have a choice then. You come back flying with me and we cure you of your fear or you don't attend his wedding, which is it to be?" Castiel asked, his tone returning to his normal 'I'm not taking any rubbish' one as he crossed his arms.

"I can't not go." Dean replied still not opening his eyes.

"Then its looks like you and I will be spending a lot more time together then. When's the wedding?" Castiel asked, wondering just how long he had to get Dean over his fear of flying, because failure was not an option in his mind. He would get Dean ready to get on that plane and go to his brothers wedding, oh he might not do it happily, but he would do it. Without having to be sedated.

"Two months." Dean replied, though it sounded more like a question as he opened his eyes to look at Castiel. Could this guy really do that? Get him okay to get to his brothers wedding?

"Right two lessons a week I think start with don't you? Book him in before lunch, I don't want puke all over my angel." Castiel snapped at Gabriel who had just stood there throughout the whole conversation smirking at him. His brother could deal with the man now, he was after all the one dating the guy. With that Castiel stormed back to the hanger to go and sort out his angel after her short flight.

After Castiel left Dean sat there regaining his equilibrium. Once he finally found that he was able to he straightened his head only to find that Gabriel was leaning on the desk staring at him

"What?" Dean asked defensively.

"Nothing, just don't think I have ever seen Cassie so caring." Gabriel replied contemplatively with a shrug. To be honest he hadn't seen that side of his brother for a very, very long time.

"Yeah well he wasn't that bad in the air either." Dean said running his hand over his face and through his hair. Finally adjusting to being back on solid ground.

"Is that so?" Gabriel asked with the raise of an eyebrow. Well, well this is certainly interesting.

"Yeah, well once he had got the whole you're dating my straight brother thing out of his system. Care to tell me why I'm dating Cas' straight brother?" Dean asked, well he was here he might as well get answers from the guy opposite him, and he was feeling much better now.

"Cas is it? And as for dating me, I want to make him jealous." Gabriel replied with a smirk making Dean frown. What?

"Why? And why would dating me make him jealous?" Dean asked he was seriously confused now.

"I told you last week he likes you, but he needs more than a one night stand. So I'm making him jealous so he realises this." Gabriel explained with a shake of his head. Was this guy blind or something? It was obvious that Cassie liked him.

"Who says I want something more than a one night stand hu?" Dean argued making Gabriel just look at him with disbelief. And continue looking at him until he caved. "Fine. I wouldn't say no to a relationship with someone, but I don't even know him." he tried to argue.

"Hence dating me. While you do that you are off limits to him and as such he'll have to actually talk to you, as a friend." Gabriel replied as if it really was that simple. Dean couldn't quite believe what he had just heard. I mean really?

"That's your plan? That's crazy!" he screeched.

"And?" Gabriel asked, it may be crazy but it would work, he was sure of it.

"How the hell did I end up getting involved in this?" Dean asked closing his eyes once more, though this time more due to the headache he could feel coming on due to Gabriel's craziness. And here he was thinking only Cas was the crazy one in this family.

"Its good for you Dean-o. Mischief keeps you young." Gabriel replied with a smirk and a waggle of the eyebrows which just made Dean groan, what had he gone and gotten involved in this time?


	10. Chapter 10

**Hello my darlings. I would like to thank ElleLisa22 and Little Cinch for the wonderful reviews. I would also like to thank all the people who have followed and favoured this since my last update.**

 **So here we are, the next chapter I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Dean had been gone about half an hour before Castiel did as Gabriel had expected him to and stormed into the office. Rather than throwing himself into a chair as he normally would he moved so he was leaning on Gabriel's desk his face rather close to his brothers as he asked with a low growl "What's your game Gabriel?"

"I have no idea what you are talking about." Gabriel replied amicably sitting back and linking his hands calmly and smirking at his brothers reaction.

"Don't be an ass." Castiel snapped leaning back and crossing arms so he could glare at his brother once more.

"Well I suppose that is better than assbutt." Gabriel replied conversationally he was not going to rise to his brother, and it really was rather fun seeing Cassie this pissed. Or at least it was as long as the fists didn't start to fly.

"I'm being serious Gabriel." Castiel ground out through gritted teeth.

"So am I. What is it I have done that offends your delicate sensibilities so much this time?" Gabriel asked leaning forwards now. He really didn't want a black eye.

"You are playing with Dean." Castiel spat at him making Gabriel's eyebrow raise.

"Well now, that does bring images into one's mind does it not?" He smirked suggestively to Castiel.

"Gabriel. I want to know why you asked him out." His brother demanded slamming his hands down on the desk in front of Gabriel so there faces where practically touching.

But Gabriel was not going to be intimidated by his younger brother thank you very much.

"I'm pretty sure we've already had this conversation. I think he's hot." He stated clearly so there could be no mistaking his words.

"No you don't." Castiel growled at him.

"Excuse me? Since when could you read my mind?" Gabriel asked with that tone of voice of his that told Castiel he needed to be careful, that he was skating on thin ice right now, making Castiel lean back from the desk and give his brother some space. Gabriel was after all not someone you wanted to piss off, like ever. For all his laid back attitude Castiel was well aware that when angered Gabriel was vicious. Of course that didn't mean Castiel would stop with his questioning.

"You're straight so I ask again what the hell is your game? What's your angle this time? Cos I know you have one." Castiel demanded crossing his arms once more. He would get answers from his brother somehow.

"Really? Well you'll just have to watch and find out then won't you?" Gabriel smirked at him before dismissing his presence and going back to the paper work he had been doing before Castiel had come in.

"Or I could take Dean from you." Castiel threaten, though they both knew it was empty. If there was any chance that Gabriel did actually like Dean, Castiel would not interfere in that respect. He had too much honour to do that and they both knew it.

"Good luck with that." Was Gabriel's only response not looking up from his work.

"I hate you Gabriel Novak." Castiel snapped and Gabriel could almost feel his wish to stamp his foot at his brother's insolence at not doing as he wished him to do. It really did make Gabriel smile, god how he loved pissing his brother off on occasion, and by on occasion we all know he means most the time.

"Yes I'm sure you do right now, the question is Castiel, why do you hate me?" Gabriel asked looking up at Castiel with the raise of his eyebrow once more. At that Castiel could think of no reply because he really didn't understand why he cared about this so much, so instead of responded he stormed out of the office and back to the hanger. Five minutes later Gabriel heard the plane take off, at that point he leant back with a smirk on his face. Yes his plan was going very well.

* * *

Castiel stormed back out to his beloved plane and got in preparing her for take-off but he didn't start her for a good few minutes. He knew better than anyone to not fly when angry and as such he took the time to calm down. He had no idea what was going on in his head, why this Gabriel thing bugged him so much, oh academically and logically he knew he was bugged because it made no sense, and he didn't like it when things made no sense, but that didn't explain his emotional reaction to the news. The only reason he could come up with for that was the fact that he himself found Dean rather attractive as well. But even if he wasn't dating his brother Castiel knew nothing could happen between him and Dean. It would be a little awkward to say the least to have to keep seeing each other after a one night stand. No he preferred to never see his sexual conquests again thank you very much. Life was much simpler that way, so no he wouldn't have gone near Dean until the lessons had run the course at any rate. Of course now his brother was dating him he wouldn't go near him full stop. But…

Argh this was getting him nowhere. He needed to calm down and stop thinking about Dean Winchester and Gabriel Novak. With a deep breath Castiel did just that and calm enough he started his angel and flew away. As soon as the wheels lifted from the ground he felt the peace he always craved settle on him. Up here there were no worries, no difficult emotional crap. No, up here there was just him and his angel souring together as one. Everything made sense up here, everything was clear. And fly was as natural to him as breathing. Yes up here he could find his peace and clear his mind. And for the first time since returning Dean to the ground Castiel smiled as he flew, singing the words to 'Danger Zone' by Kenny Loggins under his breath and of key as he executed moves which would have left the most confident of fliers feeling queasy had they been accompanying him. Pushing his angel to her limits as he performed the intricate dance in the sky.


	11. Chapter 11

**Hello again. So here we have another chapter for you today. Hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

When Castiel returned to the hanger he had calmed, not that he was going to let his brother know that, but he had. He didn't care anymore what he did, or at least that was what he told himself. Instead as he cleaned his angel he turned his mind to trying to think of ways he could get Dean to relax in the sky. He wasn't really sure how to get someone over the fear of flying, but he would find a way. Maybe he should find out what Dean liked, what would make him relax in the cockpit? Of course the easiest way to do that he guessed would be to ask Gabriel, but there was no way he was going to do that, no he was going to avoid talking to that man for as long as humanly possible. Hmm, he would have to sneak a look at Deans file instead. With that decided he nodded and flipped the radio he had in the hanger onto his favourite rock station as he got to work tuning up his plane. He would have to wait until his brother had left for the day before going to get it so he might as well make use of the time.

* * *

Gabriel had heard the plane return and had been waiting to see what Castiel would do next. But rather than enter the office he heard his brother switch on his radio which was a sure sign to Gabriel that he would be incommunicado for a while. He always liked his music while he was working on the plane. Gabriel was about to go into the hanger and see if they could talk but thought better of it. If Cassie wanted to talk he would come to him, and he was doing this for his brother. He would understand eventually. With that he went back to his work of trying to organise advertising for their company with no money.

* * *

Once Dean had left the airfield he had gone back to his garage, though not to work. No he instead just went and sat in his office as he tried to work out just what the hell was going on with the crazy Novak's and why in the hell he kept going along with their freakin' plans. I mean he wasn't crazy, was he? Well he must be as he kept agreeing to do stupid things, but this had to top the list. I mean dating a guy who was straight, and had a girlfriend for Christ sake, just to make his brother jealous? And let's be honest for all Gabriel's belief, Dean didn't agree with his assessment that Castiel felt that way about him anyway, I mean how could he? That guy was sex on legs, he could have anyone, why would he want Dean? So there really was no point with this ruse.

And yet he was still going along with it. He could have told Gabriel no but he didn't, so what did that say about him? Oh god he didn't have a secret thing for the guy did he? A quick analysis of his feelings confirmed that no he did not have any sort of sexual feelings for Gabriel. Which was good, very good. It seemed the only Novak Dean like was Castiel. So why was he doing this? Of course his reason was that he didn't want Castiel to know he had feelings for him, but surely he could just hide them, he didn't have to date Gabriel did he? No he didn't. So the solution was simple. He would call Gabriel and cancel. With that thought he picked up his phone, but rather than dialling the number he just starred at it. If he cancelled the date, would that make things awkward for his lessons? Cos while he had decided that the guy was definitely crazy and he had no feelings for him, Gabriel wasn't all that bad. But if he cancelled their 'date' would he have to pretend like he didn't want to talk to him or something? Oh god why was this so god damn complicated he thought resting his head on his desk and closing his eyes as he tried see a way out of this mess that Gabriel had created, though he had gone along with it. Okay, so he couldn't cancel cos that would be awkward, but he couldn't keep dating the guy cos that was just weird. So He would take Gabriel out for a drink tomorrow night and that would be it. Just one date, and then it would all be over. Okay he could do one date, and at least he wouldn't feel guilty about making Gabriel pay for it. The guy could definitely afford it multimillionaire that he was.

* * *

Gabriel left the office as he always did at 6 o'clock that evening. He even came into the hanger to say goodbye, not that Castiel gave any hint of registering his presence. But as soon as he had left Castiel snuck into the office and searched for Deans file. It took longer than he thought it would, mainly because he didn't do any of the paper work in this place and as such had no idea where it was kept, but he found it eventually and opening it up he realised there really wasn't that much inside. Only one sheet of paper containing personal information. His name, which he already knew thank you, his date of birth which informed Castiel that he was only two years younger than him, though why he needed to know that he didn't have a clue, and his occupation, mechanic and owner of Winchesters auto body shop. That could work. As a mechanic Dean would be interested in engines. Yes Castiel could work with that. With his mind coming up with various ideas that revolved around that theme he placed the file back where he found it and left the office, locking it behind him before returning to his plane to sit and think of the best way to use Deans occupation to get him to relax in angel.


	12. Chapter 12

**Hello my angels. I would like to thank Little Cinch and SuperGirlFan for the lovely reviews. I would also like to thank those of you who have followed and favoured since my last update. You are all awesome.**

 **So here we are, the next chapter, I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel spent the next day actively avoiding his brother. He still hadn't said a word to him. But 5.50 that evening found him marching in to the office only to find it empty. He knew his brother hadn't left yet so he guessed he was in the head. With that realisation he made his way over to his brothers chair and plonked himself down in it. When Gabriel didn't return within minutes of Castiel sitting down he found himself getting bored, and as such pulled the appointment book that was open on the desk towards him, and leaning back with his feet up on the desk (cos that would really piss Gabriel off) he started to read. It was a complete coincidence that the book covered his face.

* * *

Dean pulled into the parking lot of the airfield still not completely sure he believed he was doing this. But he was here now so he might as well get it over with. As such he pulled himself out of his baby and straightened his new shirt (he had decided he should make some sort of effort for this night out, he had to keep up the pretence after all, and it had nothing to do with the thought at the back of his head that might see Castiel and therefore wanted to look good at all) before he headed to the office of Heavenly Flight Training Company to go collect his 'date'.

Walking into the office Dean saw Gabriel sitting behind his desk with his feet up reading the appointment book. Or at least the quick glance which he afforded in that direction informed him that someone was sitting at the desk and he presumed it was Gabriel as it was his desk.

"Okay lover-boy let's get this done." He said with a confidence he didn't feel.

"I'm not sure that is appropriate Dean. You are after all no doubt here to pick up my brother. And I doubt we have the time." Castiel replied as he lowered the book and smirked at the shocked look on Deans face.

"I... Ur... Um... " Dean tried to answer. Yeah okay he had been subconsciously looking round for the guy but that didn't mean he expected to see him exactly, he just hoped he would, course now he had he couldn't think of anything to say, damn it.

* * *

Gabriel had been standing in the bathroom since he heard his brother make his way to the office. He wanted to know what would happen when Dean arrived and saw Castiel in there, how they reacted when he wasn't around, and as such he leaned against the door and waited. And what he heard had he chuckling to himself. God could they be any more obvious? But be that as it may he should probably go out there and rescue Dean from his brother.

"Well hello Dean-o, don't you just look divine." Gabriel interrupted, sauntering into the office from the bathroom where Castiel noted he had obviously been changing his clothes as he was now wearing a smart blue shirt that brought out the gold in his eyes. He was obviously making an effort for Dean, which would have confused (and maybe pissed off) Castiel had he cared. And he didn't, not at all.

"Thanks." Dean murmured for more than just the compliment, he was glad that Gabriel had arrived before he had made an even bigger fool of himself in front of Castiel. Then of course he remembered they were supposed to be on a date. "Um, you look awesome too." He said cringing at the lameness of that sentence.

"Well aren't you just a charmer." Gabriel replied with a chuckle as he went over and patted Dean on the cheek before turning to his brother with a smile which quite clearly stated he was the cat that had got the cream. "We're heading out now. I'll see you tomorrow, but don't worry if I'm late, I have a feeling I'm going to have a good night tonight." And with that Gabriel turned Dean and pushed him out the door leaving Castiel glaring at their backs.

* * *

Climbing into Dean's car Gabriel noted how clean and tidy it was. The car was obviously loved, but then didn't Dean call it his baby? He was about to ask when Dean turned the key in the ignition and the rock station he was used to hearing from the hanger came blaring out of the speakers.

"Wow you two really are made for each other." He murmured.

"Sorry." Dean said reaching to turn it down. "Did you say something?"

"Just that you and Cassie seem to have the same taste in music, Dean-o." Gabriel responded sitting back to see where Dean was taking him. He had a plan for this evening, and it involved mentioning his brother as much as possible. Anything he could do to make sure Castiel was never far from Dean-o's mind and hopefully convince the man that Cassie really was into him, though Gabriel had a horrible feeling that that could well be an uphill struggle with Dean Winchester.

* * *

Castiel contemplated following his brother and his date once they left but decided against it. He had decided he didn't care and didn't want to get involved. Therefore following them was not on the cards. So instead he stayed in the office a few minutes longer, giving them the chance to leave, before making his way to his car and driving back to his small and depressing one bed apartment. Of course as soon as he walked through the front door all he wanted to do was leave again. Hmm, maybe he should get a pet, you know something to come home to? Perhaps a cat, he liked cats, they were independent and did as the pleased, much as he himself did. But that didn't help right now and Castiel couldn't put his finger on the problem, (well he could if he actually thought about it but he had resolutely put Gabriel and Dean from his mind). What he did know was that he didn't want to be alone, with that he grabbed his keys and wallet and walked back out his door. He needed a beer in calm surroundings where no one would question him, and he knew just the place.


	13. Chapter 13

**Hello my lovelies. I would like to thank rainystv and Little Cinch for the lovely reviews. I would also like to thank those of you who have favoured and followed since my last update. You are all awesome.** **Also I would just like to mention that I have just started using twitter. So if you wish to follow me to get updates on my writing, or just random rubbish from my mind, or hell want to shout at me for not updating enough, you can find me at angelCastielrtw. Come along and say hi.**

 **Any road, here's the next chapter, enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

Dean took Gabriel to his local bar. It wasn't like it was a proper date so he might as well be relaxed after all. Walking into the Roadhouse he was greeted by Ellen like a long lost son, the joys of having her daughter working for him at the garage he guessed. She then turned her very astute (she had taken note of the new shirt) eyes onto his companion and her eyebrows rose. The man with Dean was not his normal taste in men, not at all. Hmm, just what was going on here?

"So Dean are you going to introduce me to your friend?" She asked leaning across the bar and pinning Dean with a glare that clearly said and explain your relationship with him in great detail to me immediately.

Gabriel of course standing next to Dean caught the look and found it highly entertaining, as such he just stood there and waited for Dean-o to reply. He really wanted to see what the guy would say about this situation.

"Oh umm, Ellen this is Gabriel, Gabriel, Ellen." Dean replied somewhat startled by her expression. I mean nothing was going on being him and Gabriel so why was she looking at him like that?

"Nice to meet you Gabriel. So Dean, how did you to meet?" Ellen asked smiling at his companion and glaring once more at the boy she had in some way started to think of as her son. If nothing else he looked after her Joanna Beth like a big brother, the least she could do is return the favour by being a sort of mother to him and Sam.

"Well, he kinda owns the flight company that sum's making me go to for lessons." Dean explained somewhat alarmed by her look, what was going on? Since when did he get quizzed as soon as he walked through the door with a friend?

"But I thought that the guy who owned that was called Castiel?" Ellen replied narrowing her eyes at him. He wasn't going to pull a fast one on her, she had heard all about it from both Jo and Sam when he and Jess had been in the bar the last evening.

"Yes well..." Dean said rubbing the back of his neck not sure how to explain exactly who Gabriel was. I mean how do you tell people that he was a multimillionaire taking a sabbatical to help out his brother?

"He's my brother and the one Dean-o here has a massive crush on." Gabriel interrupted catching on quickly to what was going through Dean-o's mind and really not wanting everyone who didn't already know, know who he was. He liked the anonymous feel that being with Dean and his friends gave him. Not one of them had any connections in the world he lived, and as such had no idea who he was. It really was refreshing in his mind.

"Gabriel-" Dean started to say with a glare at the man with him. He did not want people knowing…well anything if he was honest, about the mess he had got himself into this time.

"What? It's what Ellen wants to know, right?" Gabriel replied in an innocent voice while simultaneously smirking at him, wow that was actually a rather impressive feet.

"Yes, as well as if he has a crush on your brother, why he is out with you?" Ellen interrupted before Dean managed to put a muzzle on this Gabriel. Though she got the distinct impression that even if he tried, Dean would not succeed. It seemed that Gabriel was nothing if not determined to get what he wanted, and knowing people as she did, she would say that while he may be sweetness and light, laughing and joking as he now was, underneath that façade Gabriel was not someone you messed with, and she also would bet the bar that he was a lot more than he seemed. A lot more.

"Well now, that is a story. And one I think requires a drink to tell."

With that Gabriel sat down on the bar stool and smiled up at Dean who just groaned. Great, once Gabriel had finished here everyone would know just how crazy he was, but he knew there was nothing he could do but go along with it. Hmm, maybe he should have taken Gabriel to somewhere that he didn't know all the bleeding staff.

Ellen laughed at Gabriel, yes she liked him, he was tough, as such she nodded and got to beers for the boys before settling down to be entertained by the tale, and by Deans blushes, which she had to admit were some of the finest she had seen in quite a while.

* * *

Castiel decided to walk to the bar he had in mind, it wasn't that close but it also wasn't that far away. What he liked about it was the atmosphere. Even he, a stranger, was welcomed by the owner's warm smile. The woman also seemed to know when her customers didn't want to talk and as such left him alone to his drink, which in his mind was the best attribute of a bar. He liked to remain anonymous when out alone. A habit picked up from years of sneaking of to gays bars alone on leave that he didn't particularly want to give up (not the sneaking but the anonymity). Why would he want to know after all? He liked his simple life which had just him and his planes, and well Gabriel but he was not someone he wanted to think about right now thank you very much.

With that he pushed open the door to the Roadhouse only to be greeted by the sound of raucous laughter from by the bar. Turning to glare at whoever it was who was disturbing the peace of this place he saw the two people he was trying really hard not to think about. Gabriel and Dean. And watching them he felt a stab of pain in his chest area he didn't understand. Because while the two were not touching they were sitting facing each other on the bar stools, their knees only millimetres apart and Gabriel had obviously said… something, because Dean was bright red and yet his eyes never left his brothers. The imagine in front of him made him feel, he wasn't sure, but he thought that for the first time in a long, long time he felt…truly alone. Which made no sense, he was happy on his own, and hell he preferred it that way, so why? He didn't know the answers to these questions and quite frankly right now he didn't care. He just wanted a drink in peace and quiet and he wasn't going to get that here, with them. With that realisation he turned and left, but not before he saw Gabriel lean over and rest his hand on Dean's arm as he said something into his ear that was not for the owners hearing.

* * *

Gabriel had been telling the tale of how he and Dean had ended up 'dating' to Ellen when he saw out of the corner of his eye the door open. Who he saw framed there was a surprise to say the least. He had not expected to see his brother this evening. Had Castiel followed them? Or had he just stumbled upon them? Though this bar wasn't that close to his apartment it was within walking distance and knowing Castiel as he did, he wouldn't visit a bar within a stone's throw of his home. That just wasn't him, it wasn't anonymous enough. But either way here was the perfect opportunity to make his jealously plan work. So he rested his hand on Dean's arm and leaned over to whisper in his ear.

"Seems Cassie just couldn't stay away."

"What?" Dean asked automatically turning towards the door to see that it was closing and there was no Castiel in sight. He turned back to Gabriel with a glare at such a childish trick.

"He was here, now he's not." Gabriel said with an unrepentant shrug when he saw that look. He didn't care if Dean believed him, though he did take satisfaction in his reaction to the idea of his brother being here.

"Oh." Dean replied, not sure whether to believe Gabriel or not. I mean the guy could just be winding him up for all he knew, he seemed to like to do that.

"Disappointed? Would you prefer it was my brother sitting here stroking your arm?" Gabriel asked with a smirk as he put actions to words making Dean growl at him and shake of his hand.

"Shut up Gabriel." He replied grumpily and turned to drink his beer, Ellen having gone off to serve the other customers.

"Oh come now Dean-o, you have to show me a good time so that I will go out with you again." Gabriel said cheekily to his 'date'. He didn't know about Dean but he was having a fabulous time.

"Yeah that ain't happening. I may have been crazy once, but not anymore." Dean replied vehemently. There was no way on this earth that Gabriel was going to get him to go on another date with him, no way in hell was that happening, ever and ever and ever.

"We'll see." Was all the other man replied with a chuckle as if he knew something Dean didn't. But before he could question Gabriel on it (or think about whether he truly wanted to question him) Gabriel turned the conversation onto tales of his and Castiel's childhood adventures, making Dean smile at the thought of the Novak brothers as kids getting up to mischief. Or Gabriel getting up to mischief and Castiel somehow getting the blame at any rate. As such they spent a pleasant evening as friends, and by the time it was over Dean had forgotten all about Gabriel's threat to get him on a date again. Which let's be honest as this is Gabriel, was a big mistake.


	14. Chapter 14

**Hello again. So here we are, time for a bit of Cassie's perspective, don't you agree?** **I hope you like the guest star.**

 **Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel stormed out of the Roadhouse shaking the image of Gabriel and Dean from his mind and went instead to the next bar on the block, which strangely happened to be a British one. He had been stationed with some officers from the RAF while on more than one of his many tours and they had introduced him to their brand of alcohol, as such he knew just what to order when he walked through the door and was confronted with the bottles on the shelves.

"A large Glencraig whiskey please." He growled at the barman slamming money onto the counter. As soon as the drink was in front of him he picked it up and downed it, nodding at the barman to pour one more.

"Well I was going to say you had good taste in liquor, but if that is the way you are going to treat honey such as this I feel I may have to re-evaluate my opinion." Said the British accent of the man who was sitting on the bar stool nearest him. Turning to growl at him to shut up he was confronted by an older man with brown hair and wearing a black suit and red tie, a smirk on his face. Before Castiel could speak though the British man continued. "You know kitten, if you just wish to get drunk I would recommend the Bell's. It does the same job and is much cheaper and less of a sacrilege."

At that Castiel glared at the man and replied a short "Noted." Before downing the second whiskey put in front of him and gesturing for the barman that he wished a refill. The man next to him sighed and took the filled glass away before he could even reach for it.

"I will give you this back if you promise to give it the respect it deserves. If you wish to vent? I am all ears, or not, your choice, but I will not see you malign such nectar with your base American taste buds, is that understood?" He said in a stern voice as if he was talking to a wayward child. Castiel couldn't believe it, he really couldn't.

"Give me my drink, now." He growled in his most threatening voice. He didn't want to get into a fight over alcohol but this man was trying his patience.

"My, my, what a temper you have their kitten. I think you should try to work on that." The British man replied completely undeterred by his ominous presence. Either this man was extremely stupid or… he was not someone you messed with. Castiel had sized up his fair share of men before and this one, he just couldn't quite put a definition to. Oh well only one way to find out.

"I will kill you." He said in a low and icy voice which usually sent all who heard it running for the hills. Well except Gabriel who, let's be honest, he had learnt it from.

"Yes I'm sure you will. And though many have tried, none have yet succeeded. Let's try this again shall we? The names Crowley, who would you be kitten?" Crowley asked pleasantly still holding Castiel's drink hostage. He could have ordered another but he would not be bested by this…man. As such he remained silent just glaring at the man for all he was worth hoping to make him uncomfortable. "If you wish for me to return your beverage I would suggest you answer the question." Crowley signed when the man next to him remained silent. Did this boy really think he would scare him?

"Castiel." Castiel finally growled out realising he was never going to win against this man. He was without doubt in a league of his own.

"There now that wasn't so hard was it?" Crowley said slightly patronisingly as he returned Castiel's drink to the bar in front of him before he continued. "Now, what has got your panties in a twist then Castiel?"

"My brother and his date." Castiel replied despite himself and through gritted teeth, he really didn't want to talk about it, but he knew that if he didn't this man would make him. Somehow. He was that sort.

"Oh? Is that because said date is not good enough for him? ...or is it because you want said date for your own?" Crowley asked seeing right through the man next to him. Oh he had seen it all before and a lot more besides. And as much as he really didn't care, though this boy looked like he needed some advice. And that was something Crowley had in spades.

"Doesn't matter what I want. He's with him now." Castiel replied finishing his whiskey on his second swallow this time making Crowley think he was definitely making progress and as such didn't comment when the barman filled the glass once more.

"Very true. So what are you going to do about it?" Crowley asked. Time to see just what kind of man Castiel was, oh he had an idea. He looked the principled, honour bond sort, what with the obvious military stance, but you never know, he could be wrong. Crowley doubted it, he was rarely wrong, but it was always best to make sure.

"Nothing." Castiel replied taking only a sip of his whiskey this time making Crowley smirk. He knew that Castiel wanted to once again down it but he was restraining himself, unconsciously showing the strength of his resolve.

"Nothing? As jealous as you are? Now I'm intrigued, are you really that selfless?" Crowley asked in a mocking tone.

"I'm not jealous." Castiel snorted, I mean what did he have to be jealous about?

"And I'm an angel. Please, you don't have to lie to me kitten. I can see right through you." Crowley replied a honey coated voice. Castiel was so oblivious it was almost funny, really.

"What do I have to be jealous about? Yeah Deans hot, but he's just a hook up." Castiel replied offhandedly as he took yet another sip of whiskey.

"But is he?" Crowley asked in his honeyed tone designed to slip through any defences.

"Hu?" Castiel turning to him. What the hell was this man talking about?

"You said your brother was dating him correct?" Crowley explained with a roll of his eyes. Was this guy really that dumb?

"Well, yes." Castiel replied, what had that to do with anything?

"Then he is not just a hook up for him, is he?" Crowley explained as if it was the most obvious thing in the world making Castiel frown down into his now empty glass.

"You are not going to find the answers there kitten, believe me. But if you want my advice, become besties with this Dean." Crowley continued when he saw the look on the other man's face.

"Besties?" Castiel asked, I mean really, what the hell did that mean?

"Yes. Best friends, best buds, bff's?" Crowley rattled off.

"Why?" Castiel asked, I mean really what would that achieve?

"Oh I don't know. Maybe then you will be there to pick up the pieces when it all goes horribly wrong? Why else." Crowley replied with a smirk.

"Why would it go wrong?" Castiel asked once more. This man didn't even know Gabriel or Dean. How could he say it wouldn't work out? Even if secretly that was what Castiel wanted?

"Do you think your brother could love this man?" Crowley asked him seriously. The vibes he had been getting off of him told him that the answer to that question was no, but his question had caused a doubt to rise in his mind.

"I don't know, had you asked me that half an hour earlier I would have said no, but now… I just don't know." Castiel replied with a sigh, he might as well be honest with the guy. For all he had pissed him off when he had arrived he didn't seem so bad. Not really, thought Castiel was still wary of him, he had that vibe he had learnt to detect being round his brother, it was one of supressed power. Thinking about it he wondered briefly why Gabriel had never made something of himself with that talent but that was not of any consequence right now.

"Become Dean's friend Castiel. That way you are showing your brother you support him, family is important. Even if they have the thing you want the most. It is important to be there for them, to support them. If you take nothing else from this conversation kitten take that. That family is the most important thing in the world. I should know, I don't have any." With that Crowley smoothly got up from the bar and placed some notes from a bundle on the bar and walked stately out of the door without looking back once leaving Castiel to frown over his half-finished glass of Glencraig which he was now sipping to saviour the taste as he thought over all the strange British man had said. However much he didn't want to admit it, the guy did have some good points and gave him much to think about.


	15. Chapter 15

**Hello my darlings. I would like to thank Little Cinch for the lovely reviews. I would also like to thank all you lovely people who have followed and favoured since my last update.**

 **So here we are the next morning.**

 **Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

The next morning Castiel woke up earlier than he normally would and as such got the luxury of lying in his bed and relaxing before the start of the day. Of course his brain woke up at that point and started buzzing at him. First it reminded that today was the day of Deans next lesson. He still wasn't 100% sure how he felt about that. The next thing his mind brought up was the last thing Crowley had said to him the night before. That family was important. And however much Castiel tried to deny it he knew the man was right. In which case he was going to have to make up with Gabriel. At that he sighed. He hated it when he had to admit he was wrong, especially to his brother, and to him it seemed to happen far more than Castiel would like. But be that as it may he had been wrong and childish in his behaviour towards Gabriel and Dean. Okay he still may not like the idea of them being together, but he was just going to have to suck it up. With that and a groan he pulled himself from, his bed. If he was going to make up to Gabriel he had better come bearing a peace offering of some sort.

* * *

Gabriel woke early as well, but he bounded out of his bed rather than lazying in it as he pulled his phone to him and dialled a number whilst whistling to himself.

"What?" came a decidedly grumpy voice down the phone. Hmm, he guessed that Dean-o wasn't a morning person then. He would definitely get on well with Cassie. His brother also did not do mornings if he could help it.

"Now is that anyway to greet the new love of your life Dean-o?" He smirked down the phone making sure he sounded as upbeat and chirpy as he could.

"What the hell do you want?" Dean groaned at him down the line as if this was his worst nightmare.

"I need you to pick me up and drive me to work." Gabriel replied as if it was obvious.

"Why?" Dean asked extremely confused. Surly Gabriel did not need him to chauffeur him around.

"Because I left my car there last night when I got into yours." Gabriel explained with an eye roll. Why did he think?

"So? I'm sure you have a garage full of others, or you could just get a taxi." Dean grumbled back. There was no way he was going to be going anywhere near that airfield until he had too.

"True to both, but I went on a date with you Dean-o. Don't you think it would be nice to drive me to work after our night together?" Gabriel asked suggestively making Dean realise just what he wanted to imply with Dean dropping him off.

"I'm not that cheap Gabe. I don't have sex on a first date." he said adamantly.

"Pity it was fantastic." Gabriel replied in a melodramatic voice laced with amusement.

"You worry me, you know that?" Dean asked conversationally, he couldn't believe he was still even listening to this conversation. Why hadn't he hung up yet?

"Does that mean you'll come pick me up and drive me to work then?" Gabriel asked cheekily, he was pretty sure he knew the answer, but maybe he could wear the man down. After all, nothing more likely to get Cassie's blood pumping in jealously than seeing Dean-o drop him off after a night of passion.

"No. And no more dates Gabriel. I Mean it, its over." Dean demanded, though he had a horrible sinking feeling that it would do no good. That Gabriel would do as he wanted, screw everyone else's wishes.

"I'm heartbroken." Gabriel replied dryly as he chuckled to himself.

"Whatever, I'm hanging up now." And with that the line went dead. Gabriel smirked evilly at the phone in his hand. Oh Dean-o, you really have no idea do you?

"Should I even ask?" came a woman's voice from behind him filled with an amusement that matched his at his antics, she only heard his side of the conversation but it was enough.

"Probably best not to." Gabriel replied turning to see the most gorgeous creation on earth, or at least in his opinion, leaning against the door frame in only a red negligée. Walking over to her, he pulled her into his arms before kissing her passionately. After that both he and his girlfriend were slightly late for work, but at least she did give him a lift to the airfield.

* * *

When Castiel arrived he saw that Gabriel's car was still in the same parking space as it had been the previous evening, though to be fair his brother could have just parked there again. Though his suspicions that Gabriel hadn't come back to get it were confirmed when he got to the office and found it locked. Juggling the items he had in his hand he finally found his much unused keys and opened up. Walking into the office he placed the coffee he had purchased for his brother from his favourite coffee shop down on his desk and then straightened the appointment book he had left carelessly tossed open the last evening. Standing back and nodding he decided that that would do for now and as such went out to the hanger so he could get ready for the day. Though he did leave the door to the office open so he would hear when his brother arrived. He refused to look at the time, not wanting to even think of reasons that Gabriel could be late after his date the night before.

* * *

Gabriel walked up to the office door with a smug grin on his face and his hair still wet from the shower. Though the smug look fell when he walked through the door and saw a coffee cup on his desk. What the hell?

"Good morning Gabriel. I brought you a coffee." came Castiel's voice as he walked through from the hanger, and in a surprisingly pleasant tone. Just what was his little bro up to now?

"Why?" he asked approaching the cup with caution as if it would explode at any moment.

"I had it brought to my attention that I may have been a bit of an assbutt to you about Dean." Castiel replied still amicably.

"By who?" Gabriel asked completely confused. He had never seen his brother listen to... well anyone. If anything he usually did the exact opposite of what people suggested.

"A man I met last evening." Castiel replied with a wave of his hand. The who was unimportant, he was trying to make up here.

"A man?" Gabriel asked in a suggestive tone as a smirk appeared on his face and he settled into his chair, though he still hadn't touched the coffee.

"Not like that Gabriel, get your damn head out of the gutter, just cos you're getting some doesn't mean we all are." Castiel snapped, he could only do so much being nice to his brother after all and that smirk was definitely the limit.

"Who said anything about me getting some?" Gabriel replied innocently though the smug smile he had on his face when he arrived repapered, and though it was there because of a different person than Castiel suspected, the reason was the same. He had indeed 'got some'.

"Your smug ass grin." Castiel spat at him, trying really hard to rain in the feelings he had, which he didn't understand and flatly refused to admit could possibly be jealously. Crowley may have been right about the family thing, but not about any of the rest thank you very much. He was not interested in Dean Winchester, in any way.

"For your information, Dean-o doesn't do sex on a first date." Gabriel replied trying really hard not to laugh at his brothers reactions. Oh this truly was priceless he though as he watched Castiel narrow his eyes at him and turn and march out of the room.

Once Castiel had gone he turned his eyes to the coffee cup, inspecting it from all sides before he gingerly pickled in up and studied it closer. He then pulled of the lid and checked the contents inside, smelling it just to make sure. He then took a very cautious sip. Pulling back he looked at it once more raising one eyebrow. Seemed his brother really had just got him coffee, well wonders never cease. With that he took a good long swallow of coffee before turning to the work he had to do that day.


	16. Chapter 16

**Hello my dears. I would like to thank Little Cinch and rainystv for the lovely reviews. I would also like to thank you lovely people who have followed and favoured since my last update.**

 **So here we are, next chapter. Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

Dean walked into the office of Heavenly Flight Training Company not sure if he wanted to kill Gabriel for waking him up at the ass crack of dawn or hide behind him cos he now had a lesson with Castiel who wasn't exactly happy with him the last time they spoke. It really was a 50/50 split. But be that as it may, he had a flying lesson to get to. And he needed to do this for Sammy, forget the Novak's and think of Sam. So taking a deep breath he pushed open the door.

"Well you certainly seem more awake than you did this morning." Gabriel said loudly as he walked through the door making him give him his best death glare.

"Your an asshat Gabe." He growled in response only for another voice to join the conversation.

"I prefer the term assbutt, but asshat works just as well."

Dean looked over to the voice to see Castiel leaning against the door frame to the hanger and he wondered how long he had been there. And god did he ever look amazing. He may have only been wearing simple jeans and a light blue shirt but to Dean he looked...gorgeous was the word that came to Deans mind. Though this could be less about the clothes and more about the expression on the man's face. Cos rather than smirking at him or looking at like he was some bug under his shoe Castiel's gaze seemed to be genuinely friendly. And that smile, Dean couldn't describe. It was small, barely even noticeable unless you really looked, but it was a true smile. The first true smile he had ever seen on the man's face he reckoned. He had no idea what had happened to make Castiel so drastically change his approach to him, but he certainty wasn't going to complain. No, he was going enjoy it for as long as it lasted and bask in the glow the man brought up inside of him. He was thinking these things so hard he hadn't even realised he was just standing there staring at the man until a cough sounded from the direction of Gabriel and interrupted his thoughts making a blush appear on his cheeks.

* * *

Castiel had heard Gabriel's extremely loud comment and he was all for going into the office and giving his brother a piece of his mind, but as he got to the doorway he heard Deans response and he couldn't help it. He smiled. He was so glad that Dean was not fawning all over his brother that what he had to say to him left his mind completely to be replaced with a sentence directed at Dean.

"I prefer the term assbutt, but asshat works just as well."

And then the man turned to him with those stunning green eyes of his and he just stared. So Castiel did the only thing any sensible man would do in such a situation, he stared right back. But not in mocking or challenge, but just because...well he couldn't imagine anyone not staring at such a man as Dean Winchester, he truly was an enigma. One Castiel briefly wished he could have the pleasure of unravelling.

* * *

And so they starred, and starred... and starred. Gabriel who was sitting behind his desk kept moving his head from one to the other as if he was watching a tennis match, waiting for one of them to break. It took him a minute or two, but he soon realised that if he didn't do something they would be standing staring at each other for the rest of the day. It seemed that when Dean and Cassie's eyes locked nothing else in the world existed to the two of them. Good, about bloody time. But really, they needed to stop now, he was starting to get uncomfortable. With that thought he coughed to break their concentration and was rather amused when Deans cheeks once again flamed red. Man did that guy ever blush. Turning to his brother he saw a strange look on his face. On the one hand Cassie looked like he wanted to smirk at him with a 'take that' sort of look, but on the other it seemed as if he was almost... what was that look? Was that... shame? Why would his brother feel shame about staring at Dean? I mean really?

* * *

Castiel turned to his brother when he coughed, about to give him a smirking look which said, 'oh yeah you think he likes you better than me?' But then he remembered. This man was actually dating his brother. He should not be staring at him as he had. Hell he shouldn't be thinking of him in any way other than as his brothers boyfriend and his pupil. It didn't matter how attractive he was. He was without doubt completely off limits. With that thought a small amount of shame came over him at what he had been doing, but luckily before he could actually think too much about it Dean spoke into the silence.

"Hi Castiel." Dean finally managed to get out now he wasn't staring into those blue eyes. When he did that he couldn't think, let alone talk.

"Hello Dean." Castiel replied turning back to him with a smile and once again very briefly there eyes locked before the blue-eyed man looked away as if it was of no consequence. "Shall we get started?" He asked gesturing towards the door of the hanger giving Dean the room to breathe and pull himself together a bit more.

"If we have too." He replied with mock grumpiness hoping to relieve some of the tension he was feeling in the room.

"Don't worry Dean. I have no flying planned today." Castiel chuckled in response.

"Then what are we doing?" Dean asked, cos last time he checked he was here for flying lessons.

"You'll see. Come." Castiel said turning to go out the door but not before he looked at Gabriel once more with that unfathomable expression on his face.

* * *

Once Castiel and Dean had left for the hanger Gabriel sat there frowning. What the hell was going through his brothers head now? He was supposed to be jealous then realise he wanted Dean. Which seemed to going well from what he had seen, but then that look, what was that about? Cassie was supposed to be in the getting to know Dean period. Which sure Gabriel was well aware would include a lot of flirting between the two. But that was just who they were and how they showed they liked each other, so what was Cassie's problem now? And how was he going to fix it? Did he need to fix it? I mean it seemed that Castiel was at least being nice to Dean, so maybe he should just leave well enough alone. While that sounded like a good thing to do, Gabriel hated not knowing everything that was going on. Hmm, he was going to have to keep an eye on his brother it seemed.


	17. Chapter 17

**Hello my dears. I would like to thank rainystv and Little Cinch for the wonderful reviews. I would also like to thank all you lovely people who have followed and favoured this story since my last update. You are all awesome.**

 **So just a heads up I'm not sure how much I will be able to update in August what with holidays and everything, but don't worry I won't have forgotten the story or anything, but it might take me a while to get more chapters up that month.**

 **Anyway now on with the story. Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel lead Dean to the open whatever, he would call the hood had it been a car, but well it was the plane equivalent he guessed. Though why it was open he had no idea. I mean, he was a mechanic sure, but he dealt with cars, planes where a complete mystery to him.

"So Castiel, what's with having the hood up?" He asked casually trying to push away his feelings for the guy with the bravo statement.

"Castiel?" Castiel turned to him and asked with a tilt of his head making Dean thoroughly confused.

"Yeah that's your name right?" He asked as if he wasn't completely sure of the answer, and well he was dealing with a Novak, so who knew? Maybe he really wasn't called Castiel after all?

"Yes its just… nothing." Castiel replied turning back to his plane when he remembered his decision that morning to support Gabriel's relationship. He had already stepped across one line with the staring, he didn't need to step across another with the whole nickname thing.

"No way, you're not getting out that easy. What is it?" Dean asked, anything to get out of talking about planes, or flying or anything that he was actually here to learn.

"its just last time you call me Cas." Castiel replied somewhat sheepishly looking at Dean through his far to long eyelashes making Dean think that quite frankly he would call this guy anything he wanted him to. Though he wasn't sure what he wanted him to call him.

"Sorry dude, must have been lack of oxygen.," Dean tried to joke in case the guy felt offended or something, though it didn't seem like that, it was always better to air on the side of caution in Deans mind.

"I liked it." Castiel replied moving his head so he was now staring straight at Dean who just gulped at the look in his eyes.

"Well then Cas it is." He finally replied still staring right back at the man. Cos damn, there was no way when those blue eyes where on him he could look else where. "So why you showing me under your angels hood Cas?"he asked in a straggled voice, trying to make it look like he wasn't interested in Cas. But damn he really was.

At that sentence Castiel smiled and Dean almost melted into a puddle on the floor. Castiel couldn't believe that Dean had called his plane angel, though that thought was muted somewhat by the thought of who had told him that name. because it certainly wasn't Castiel himself, which meant Gabriel must have mentioned it. though why his brother and Dean had been discussing him on there date was a mystify to him.

"I would like to explain the concept of the engine of this plane to you Dean." He finally answered the other man.

"Why?" Dean asked, cos really, why?

"You are a mechanic correct?" Castiel asked as he leaned against the plane to explain his reasoning to Dean.

"Yeah so?" Dean asked still not getting it.

"So I thought if you knew how the plane worked you would feel better flying in it." Castiel replied with a shrug of his shoulders making Dean chuckle.

"Yeah well its not like I can just pull over and fix it if breaks down though can I?" He replied shaking his head at Cas' crazy idea.

"That's why we need to make sure it wouldn't break down." Castiel emphasised turning so he was facing the engine about to start the lesson.

Dean rolled his eyes at the man's back and muttered "comforting." In a sarcastic voice. Though Castiel chose to ignore the tone.

"Yes I like to think so." And with that Castiel started to tell Dean about the engine and explain the different parts. Dean kinda zoned out of the lesson as such and just listened to what he was saying, cos in his mind there was nothing sexier than a man explaining an engine to him.

Castiel looked over at Dean when he was explaining a specific part and he saw that his eyes were glazed over. It seemed Dean was not interested in learning how the engine of planes worked, either that or he had been distracted by something else, maybe he was thinking of Gabriel? Planning there next date maybe? That thought stabbed through him and he shoved it aside and decided it was time to take another track with this lesson.

"Okay Dean, I think it time I taught you what was what in the cockpit." Castiel said to the other man in the middle of his own sentence.

"Hu?" Dean asked pulling himself out of fantasies that involved him and Cas and cars, in various different positions, be it on them or in them.

"You heard Dean. Get into the plane." Castiel snapped at him fed up with him zoning out on him. He could only put up with so much after all.

"Okay." Dean agreed realising he had pissed Cas off and not wanting to have to explain what he was thinking about. As such he went up to the plan and got inside. Of course once there he remembered the last time he was inside this plane and his breath started coming in short gasps.

"Calm down Dean, you are going nowhere, I'm not in the cockpit." Castiel said in a calming tone as he noticed the man's accelerated breathing. He had planed to get up in the pilot seat to show Dean what was what but from his reaction he knew that that would not work. It looked like he was going to have to do it all from here. With that he leaned into the cockpit, slightly worried when Deans slightly calmed breathing speed up once more. But when it settled to a rhythm that yes, was accelerated but not worryingly so, he continued with his lesson, teaching Dean what all the instruments on the dash were for.

* * *

Dean on the other hand had calmed when Cas had said he wasn't getting into the cockpit. They weren't going anywhere, he could sit in a stationary plane right? that was until Cas leaned in with him and started pointing out different things. It was at that point Deans mind went somewhere completely different. having Cas this close to him, close enough that he could feel his breath on his face when he turned to look at him, close enough that he could feel the warmth from his body against his own. Close enough that they had no matter now much either of them moved they had constant physical contact, it was in Deans mind bliss filled torture. Hell if he could have this contact when Cas flew he doubted he would care one way or another where he was, juts as long as the guy kept touching him. Oh Dean knew he didn't mean anything by any of it, the cockpit was small and as Cas was leaning in from his side it was extremely close quarters, but that didn't stop his mind and body reacting in a certain way. Luckily Cas didn't notice. Or so he thought.

* * *

Castiel talked about the different instruments as if on autopilot, he was finding it rather distracting being this close to Dean and it took all his effort not to lean that little bit closer to the man, to whisper his words into his ear. To casually run his hand up Deans legs as he talked and make his breathing speed up once more. In fact the only thing that stopped him from playing with the man he had completely at his mercy was the thought of Gabriel. Damn his brother for ruining his fun. But even he wasn't noble enough not to take enjoyment at the accidental touches they shared, or to stop him from watching Deans every movement like a predictor watches his prey. He was after all, only human. And Dean it seemed was extremely susceptible to his actions. That wasn't his fault, and Gabriel couldn't blame him if Dean reacted in a certain way to his close presence now could he? And if he did then maybe his brother should find himself someone... else.


	18. Chapter 18

**Hello my darlings. I would like to thank Little Cinch and rainystv for the lovely reviews. I would also like to thank all you lovely people who have followed and favoured since my last update.**

 **So here we are the next chapter. I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Gabriel had been sitting at his desk for some time before he decided that he was getting nowhere, as such he might as well go and see how the lesson was going in the hanger. So making his way to the door he quietly opened it and propped himself in the doorway from which he had a perfect view of what was going on round the plane. And what he saw eased his mind somewhat. Because there in front of him was his brother leaning extremely close to Dean for some god knows what reason. And to be honest he was pretty sure that Dean had no idea either if the look on his face was anything to go by. No Dean looked like he just wanted Cas to get even closer. Chuckling to himself he returned to his desk chair and sat back to think. It looked like that part of his plan was going well and required no input from him. Cas and Dean obviously had massive crushes on each other, so the question was, what next? Hmm, maybe he and Dean should go on another date? That would get Cas' blood boiling he was sure, and he would snap at some point. Yes that was what he would do. With a nod and conveniently forgetting about Dean saying no more dates he turned back to the paperwork he was supposed to be doing that morning, rather than planning his brother's love life.

Castiel and Dean finally came in at the end of their lesson, though it seemed it had over run a bit, what with Castiel feeling that Dean really didn't quite grasp the purpose of the instruments and as such needed to take an extra-long time explaining them in the extremely close quarters of the cockpit. Perfectly reasonable excuse if you asked him. Not that it mattered, Gabriel didn't seem put out when they both returned to the office, him to get a drink for his now parched throat and Dean so he could leave. Though in all honesty Castiel spared his brother barely a second thought.

* * *

Dean followed Cas into the office still in a daze from the close proximity and the touching they had been done the last god knows how long. He watched as the man went over to the fridge and bent down to get himself a bottle of water from inside, his throat drying at the sight of Cas' ass as his jeans tightened over it. Damn it was fine.

Gabriel on the other hand watched them come in and took note of Dean's glazed expression, that was good, he could work with that. He almost laughed out loud when he watched the man's face as Cas bent over, cos it was without a doubt a complete picture of lust. Good it was about time Dean showed his feelings, he thought sarcastically to himself. But he could chuckle about that later, first he had to put on his own lust filled look for dear old Dean-o.

"Hey Dean-o, good lesson?" he asked casually making his way from his desk so that he was standing next to Dean.

"Oh yeah." Dean breathed not able to pull his gaze away from Cas who was now standing and drinking from the bottle he had collected.

"Good glad to hear it. Must get you to book another." Gabriel replied finding it really hard not to crack up at the display the two other guys in the office were putting on, whether they knew it or not. There was Cas, doing the sexy guy drinking thing, hell Gabriel wouldn't put it past him to start pouring the bottle over his head sensually any minute. And Dean, well he was just lapping up Cas' every move.

"Yeah." Dean breathed in response. He so was not listening to a word that was coming out of Gabe's mouth right now.

"And another date." Gabriel suggested innocently though there was a smirk on his face as he said the words, not that Dean or Cas saw it.

"Yeah," Dean agreed once more before the words registered and he turned to stare wide eyed at Gabriel. "Wait, what?" He asked sharply.

The sharp tone of Dean's voice also pulled Castiel out of his own amusement of winding up Dean that little bit more with sexual images. He couldn't do that, he was dating his brother. And if he was correct, Gabriel had just asked Dean out once again, but really? Hadn't he seen how Dean had reacted to him? Wasn't he worried or, I don't know, jealous or something? Or… maybe he had got it wrong? Maybe Dean wasn't interested in him and he and Gabe had just got together to wind him up making him think he was or something? He wouldn't put anything like that past Gabriel, though he wasn't sure that Dean would go along with such a plan.

"A date Dean-o, you know? Me and you together alone." Gabriel replied aware that his brother was now listening to them closely. Good.

"Umm Gabe…" Dean started to say. Trying to find a way to say not in a million years without sounding like a dick to Cas who he knew was now listening intently.

"Yes I know we only went out last night, but I just can't seem to get you out of my mind." Gabriel interrupted fluttering his eyelashes and inwardly laughing at the death glare Dean was giving him right at that moment.

"What?" Dean asked completely thrown by that sentence, cos what the hell was that son of a bitch up to now?

"So tomorrow night then? Maybe we could go for dinner? My treat of course." Gabriel suggested knowing that if he offered food, Dean was more likely to agree. It may have only been one 'date' but he had learnt a lot about Dean Winchester in that evening.

"Where?" Dean asked causally, cos let's be honest, Gabriel could afford to take him anywhere, and who in their right mind turned down a decent free meal?

"Wherever you like Dean-o." Gabriel replied in a silky voice as he gently rubbed his hand up and down Dean's firm arm. Well it wasn't like he could openly start rubbing his hands together was it? So he went for the next best thing.

"Okay." Dean nodded, already thinking of the free meal and where he would make Gabriel go. He was so caught up in these thoughts that he missed the shadowed expression that crossed Castiel face before his usual cynical mask replaced it.

"Excellent I can't wait." Gabriel replied in a rather sinister tone of voice in Dean's mind, it creeped him out and made him wonder just what Gabriel's game was here. Cos as far as he could see it him and Cas had been getting on great, so why did Gabe ask him out again?

"Right well I, umm, I had best go. See you Cas, Gabe." He got out into what had suddenly become a rather strange atmosphere. With that Dean left quickly.

Gabriel on the other hand sauntered slowly back to his seat behind his desk, and returned to his work, or at least pretended to, though he was well aware that his brother's eyes followed his every move with his intense stare. So Gabriel sat and waited for Castiel to speak and say whatever it was he had on his mind this time. He didn't really think his brother was going to stop himself, after all he had never done it before.

* * *

Castiel watched Dean agree to a dinner date and he then watched the man leave. But what he was really watching was his behaviour with Gabriel, because from what Castiel could see, they did not act like two people who were dating. Oh yes Gabriel did, he seemed to really like Dean, but Dean? He looked like he only agreed because he liked the idea of a free meal. And that wasn't right. He might not like the idea of Gabriel and Dean dating, though he still didn't know why (well not exactly and he certainly wasn't going to investigate that any further thank you very much), but he disliked the idea of someone using his brother even less. Though he couldn't say that to Gabriel could he? Not after the way he had reacted, his brother would think that he was just being spiteful, after all it wouldn't be the first time, though he did try and keep elements of truth in his words. No he had to be supportive of this relationship, it was what he had decided to do and it was what he would continue to do. Then maybe when the shit hit the fan, as it was so going to do and no doubt soon, he would be there to help his brother… and kill Dean Winchester if he hurt him.

* * *

"Okay little bro, out with it." Gabriel muttered not looking up from his paper work. He was fed up with the silence, it was obvious that something was on Castiel's mind after all.

"With what?" Castiel asked faking an innocence that they both knew he didn't have.

"Whatever bee you have in your bonnet." Gabriel replied looking up at his brother with challenge in his eyes.

"Are you sure that you want to keep dating Dean?" Castiel asked before he could think better of it. But now the question was out there he wasn't about to take it back.

"Sure why not?" Gabriel asked as if he was curious as to why Castiel would think otherwise.

At that Castiel gritted his teeth, he was going to have to say something now, something he would much rather not speak of. But here goes nothing and all that. "He was rather… flirty during our lesson." He finally got out with a shrug as if it was no big deal, when they both knew it was.

At that Gabriel raised his eyebrow in surprise and affront, oh he was sooo going to milk this one. "What? you think he likes you more than me?" He asked defensively.

"I didn't say that." Castiel snapped, though they both noticed he didn't deny the idea.

"Sooo what were you saying?" Gabriel asked folding his arms and leaning on his desk. Oh this was great, though looking at Castiel he wasn't sure if his brother was trying to get Dean from him, or (god forbid) protect him, though the last idea was hilarious in Gabriel's mind.

"Nothing just forget it." Castiel grumbled and turned to leave the office and return to his angel. He needed to clear his head, and what better way to do that than go flying.

Gabriel on the other hand was frowning, wondering for the first time if his plan really was as good a one as he had first thought. Because watching his brother over the last few minutes he had come to the startling realisation that maybe he just didn't know him as well as he thought he did. And maybe 15 years in the USAF had changed Castiel in ways that Gabriel had never really thought about.


	19. Chapter 19

**Hello my darlings. Sorry for the long absence. I would like to thank AngelwatchestheWorld, Little Cinch and Guest for the wonderful reviews. I would also like to thank all you lovely people who have followed and favoured this story since my last update.**

 **So here is the next chapter, I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

The morning after his lesson Dean sat at his desk going through paper work, or at least trying to. But he found that every few minutes his mind drifted from the figures and part requests on his desk to be instead invaded by Novak's, in one form or another.

First it was thoughts of Cas. These came in the form of Dean's mind conjuring images of him, smiling at close quarters in the cockpit of the plane as he explained something, the feel of a gentle touch on his arm as Cas guided his attention to the instruments, the image of him drinking that bottle of water… and damn did those images cause his head to go crazy, spinning round into fantasies of all that he would very much like to do with the guy before he pulled his mind back to the work on his desk.

Then the thoughts of Gabriel would intrude. And these were as different as the ones he had about Cas as chalk was to cheese. Because this time he was trying to work out just what the man was up to. You see in the hours since his last meeting, Dean had come to the conclusion that he and Cas had been getting on pretty well without Gabriel's input, in fact Dean thought that if Gabriel had kept his mouth shut he might just be having a date with the sexy Novak brother this evening. But no, Gabriel had to go and intervene and invite him out for dinner. And he couldn't say no, well he could have, but he didn't wasn't Cas to think he was using his brothers or that he had hurt him, but on the other hand he didn't want to give Cas the idea that he and Gabriel actually had a chance and therefore make the guy back off. Damn this was so freaking complicated. And then there was the fact that Dean was to have an actual dinner date with Gabriel that evening. He had been tempted to make Gabriel take him to the poshest most prestigious restaurant in town, after all it wasn't like Gabriel couldn't afford it, or they would turn the guy away. In fact the paparazzi would no doubt love to have a photo-op of Gabriel Novak with Dean on his arm, that alone had been a temptation, but after dreaming about that form of revenge for about a minute Dean had conceded that if Cas ever found out that he had done that to his brother, he would no doubt beat the crap out of him. As such Dean had decided that he and Gabriel would go to Benny's for their dinner date tonight, and when there he was going to have a little chat with the older man and find out just what the hell game he was actually playing, cos it had got to the point where Dean was really starting to question this trying to make Cas jealous to get them together plan.

"Argh, Damn it all to hell." Dean growled as these thoughts crossed his mind for about the hundredth time in the last hour and he slammed the poor defenceless paper he was supposed to be reading back onto his desk.

"That bad, hu? What's up?" Came a voice Dean knew as well as his own from the doorway. Looking up (and up), he finally found himself looking into the smiling eyes of his brother.

"Hey Sam, how you?" He asked smiling back at his brother and forcing all thoughts of all Novak's to the back of his mind.

"Uh-uh Dean. I asked first. So what's the problem?" Sam asked making himself comfortable in the chair opposite Deans anticipating that his brother was having some sort of financial issue.

"Well… I have a second date tonight." Dean mumbled, because however much he really didn't want to talk about the crazy situation he had managed to get himself into, he also needed someone's help to figure it out. And Sam was a clever bastard, surely he would have some sort of insight.

"And that's a bad thing? And hey, when did you go on the first?" Sam asked smiling at his brother, happy to see that he seemed to found someone, or at least someone he was willing to go out with for a second time. Which wasn't actually that easy, apparently.

"The night before last." Dean replied with a sigh which made Sam smirk as he put two and two together and got four, even if the answer was actually three.

"Wow, you must really like this guy hu? So where are you and Castiel going?" Sam asked just to make sure that his suspicions were right, but it wasn't like Dean had shown any interest in any other guy of late, and hey if Cas was going on a second date with him then that must mean something right?

"Castiel? Wrong Novak little bro." Dean replied with a smirk of his own as his brother's face morphed from one of happiness to complete and utter shock, at least that told Dean that Sam knew exactly who he was dating.

"What?! Your- wait what?" Sam spluttered at him in disbelief.

"Dating Gabriel Novak? Yeah." Dean replied with a nod still smirking, that look on his brothers face almost made it worthwhile dating Gabriel, almost.

"No you can't." Sam said resolutely shaking his head in denial which made Deans eyebrows rise.

"Why not?" He asked calmly wondering just what had gotten into his brother.

"Because… well for one thing he's straight and got a girlfriend." Sam argued, though he knew that while he may be a damn good lawyer, his brother was certainly going to win this one.

"And the other?" Dean asked curious now just what it was.

"I don't know what you mean." Sam mumbled feeling once again like the little boy confronted with his big brother demanding he tell him the truth.

"Sammy." Was all Dean said and then just looked at his brother until he caved.

"My company are his legal representation and he is one of our biggest clients. It's how I heard about the flight school, I was going through his portfolio and found it." Sam replied through clenched teeth.

"So what?" Dean asked with a frown. He didn't understand what any of that had to do with him.

"So one wrong word from him and it could end my career Dean." Sam explained in exasperation, surely Dean could see that.

"Don't worry, Gabe wouldn't do that." Dean replied with a wave of his hand dismissing the idea as simply as that.

"Oh my god, you call him Gabe, you've given Gabriel Novak a nickname. What the hell Dean? You were just supposed to get over your fear of flying, not screw the Novak's." Sam snapped at him for his blasé attitude to his career. Damn it, Dean could mess up everything with this.

"Okay first off I'm not screwing them. If anything Gabe is screwing me-" Dean started to say only for Sam to interrupt with a disgusted face.

"I so didn't want to know that."

"Not like that, bitch. Get your head out of the gutter." Dean replied with a frown at his brother, not so much that he went there, but more because he went there before Deans mind could and that was just the wrong way round in the elder Winchesters mind.

"Fine jerk. Then just tell me straight, what the hell is going on?" Sam asked because he was getting the feeling that this was really not as simple as it seemed. Not that it seemed that simple to start with if truth be told.

With that Dean told Sam all about Gabriel's crazy plan and all about Cas. At the end of it Sam felt like washing his hands of all three of the men in this screwed up crazy love triangle, but he couldn't because Dean was his brother, and well… 'Gabe' was Gabriel Novak. It was for those two reason that the next words left his mouth, of course once he had spoken them he wished more than anything he could take them back, if for no other reason than the hope and thankfulness he saw in his brothers eyes scared the shit out of him.

"I think Dean that I should come with you for your next lesson and see for myself what's going on at that place."

"Sounds good." Dean replied nonchalantly, but nothing could dim the look in his eyes and Sam just lowered his head in his hands as he groaned at the thought of even trying to understand the situation he had just got himself into. Why couldn't anything ever be simple?


	20. Chapter 20

**Hello my dears. I would like to thank Little Cinch for the lovely review. I would also like to thank all you lovely people who have followed and favoured since my last update.**

 **Here is the next chapter, I'm sorry, it's a short one. I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Dean drove up to the airfield later that day to pick up Gabriel. He thought he would have to go and collect him from the office but when he arrived he was already waiting for him. That alone set Dean on edge. How were they supposed to make Cas jealous if he didn't see them together? But before he could question him Gabriel got into the car and growled at him to drive. It seemed Gabriel Novak was not a happy bunny right now.

"Okay Gabe, what's going on?" Dean asked as he drove them out of the airfield and onto the road which would take them to Benny's.

"Nothing." Gabriel replied turning to look out of the window with a frown firmly in place on his face.

"Bull. Spill now or I'm kicking your sorry ass out of my baby." Dean growled back, he didn't need any more shit from the freaking Novak's thank you very much.

Gabriel was silent after that. What was going on was something he did not like to admit, even under the pain of death. He did not like admitting when he was wrong. But after his conversation with Castiel yesterday and throughout today he had been thinking, analysing and watching his brother. And he had come to the realisation that the path he was currently walking might not be the right one. That this might not be the way to get Castiel and Dean together. The only problem was he had no idea how to change the situation he had got them all into. Because from what he could work out it seemed that Cassie thought that Dean was using him and that he Gabriel really liked the guy, when in actual fact that couldn't be further from the truth.

"Gabriel." Dean snapped into the silence, pulling the car with a jerk to the side of the road and a halt. "Talk or walk."

"Damn it Dean. Fine. You want to know what's going on? Well I'll tell you, I think I've screwed up and I have no idea how to fix it okay?" Gabriel snarled at him with narrowed eyes. Though when he saw the confusion in Dean's he sighed and ran his hand over his face before taking a deep breath and trying again. "I thought that this would work, you and me pretending to date. But it's not, if anything it seems to be doing the opposite to what I wanted." He said on another sigh.

"How so?" Dean asked. Now Gabriel was talking he was going to get all the information from him he could.

"Castiel is worried that you'll hurt me because you seem more interested in him." Gabriel replied with a raise of an eyebrow and a 'go figure' look on his face.

"I am more interested in him." Dean smirked back at the older man.

"Yeah Dean-o, I'm well aware of that, thank god. But I think he thinks you're using me or something, and because he thinks this is my first relationship with a man he is being decidedly protective of me." Gabriel said with a shake of his head at the idea that he would need protecting from anyone. But it was kind of sweet of his brother he guessed, just not so helpful right now with his plans.

"So you're saying I'm not your first male relationship Gabe? I'm heart broken." Dean replied with a fake sorrow filled look on his face making Gabriel chuckle at him.

"If this was real Dean-o, you would be, never fear." He responded before going back to the serious point of the conversation. "I'm just not sure what to do now."

"You could tell him the truth." Dean suggested with a shrug. I mean that would work right?

"Err, noooo, I don't want my face rearranged thank you very much." Gabriel replied with a shudder and turned to look out of the window once more. Tell the truth? What was Dean-o thinking?

"I'm sure you could defend yourself against Cas, Gabe." Dean said wiry.

"Oh yes I could, but it would be his right to beat the crap out of me so I would have to let him." Gabriel responded with a put upon sigh at the thought of having to behave in such a gentlemanly behaviour, why did they have to be raised gentlemen? It would make life so much easier if he and Castiel hadn't been.

"Okay." Dean wasn't sure what else to say to that sentence. "So what are we going to do?" He asked instead.

"Well I suggest we discuss it over dinner, don't you?" Gabriel replied turning back to the man in the driver's seat with a sunny smile on his lips.

"Fine, let's go. But you're still paying." And with that Dean pulled the car back onto the road and drove them to Benny's.

And discuss it they did. They finally agreed on a plan, or at least the beginnings of one. The first thing they would do would be to stop the pretend dating and just be friends around Castiel, leaving Dean to flirt with him all he wanted. Then when Castiel questioned Gabriel about how he might want to date Dean, Gabriel would encourage him, telling him that he was right and he really wasn't interested in Dean in that way. And hopefully the two would get together. That decided Dean and Gabriel ended up having a rather fun evening, after all they did actually get along, and Gabriel decided to regale Dean with stories of him and Castiel's childhood exploits, which Dean of course returned with stories of him and Sam. Of course if either of their brothers ever found out about this trade in tales they would no doubt kill them both. But what the hell right? what they didn't know wouldn't hurt them as the saying goes.


	21. Chapter 21

**Hello my darlings. I would like to thank rainystv, InnerChild73 and Little Cinch for the lovely reviews.**

 **So here is the next chapter, I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel arrived at the office of his and his brother's flight company expecting to have to open up as he had had to do the last time Gabriel had gone on a date with Dean. But when he tried to door on an automatic action it opened. Frowning he entered to find his brother already sitting behind his desk going through paper work. What the hell? That wasn't right. Surely if his date had gone well with Dean he would have been out late and therefore get to work late right? Hmm, it made his suspicions that Dean was using his brother even more certain in his mind. It must have been that Dean literally just went out for dinner with Gabriel. And it wasn't like his brother was made of money or anything. This business of theirs hadn't really taken off after all, and yes Castiel was well aware that that was mainly his fault for being a grumpy assbutt. But he had found it hard transitioning from being in the air force to being a civilian. So there. But back to the problem at hand, how was he going to question Gabriel about his date without him getting prissy thinking Castiel was trying to split him and Dean up so he could have him for himself? Not that he would ever do that, but still it seemed Gabriel to think he might, which hurt actually. But now was not the time for that. No now he had to work out the right question to ask. Hmm.

* * *

Gabriel heard the door open but didn't look up. He would wait for Castiel to instigate the conversation. He knew his brother would ask how his date went, he had become rather interested in Gabriel's love life after all. Or at least his fake love life, when he had thought Gabriel was in a long term relationship he hadn't even asked the woman's name. But when Castiel didn't say anything for like a minute and he didn't hear the door close he looked up only to see that his brother was just standing there in the doorway. What the hell?

"You auditioning for the job of doorstop Cassie? Because I really don't think we need one." Gabriel said in a dry tone making his brother move and shut the outside door and walk over to the coffee machine pouring himself a cup as Gabriel watched his every move.

"So, Gabriel. How was the date?" Castiel asked nonchalantly as he poured his coffee. After all the worse his brother could do was tell him to go jump out of his plane without a parachute.

"Okay, I guess." Gabriel replied still not taking his eyes off of Castiel.

At those words Castiel turned round to him and leaned against the counter, coffee in hand and returned the stare with equal measure.

"You want to talk about it?" He asked casually taking a sip of his coffee yet never letting his eyes leave Gabriel's.

"Dean and I have decided to just be friends. There's nothing between us, romantically speaking." Gabriel replied in an equally casual tone which had every one of Castiel senses on high alert. His brother was lying to him. The question about what, and why?

"Oh? Well I would say I'm sorry, but I don't believe he was right for you." Castiel said hoping to break through his brothers walls with his statement which just oozed I told you so.

"Agreed." Gabriel replied amicably making Castiel narrow his eyes at him. Gabriel was telling the truth about that. He really did think that he and Dean weren't suited. But, he had seemed so keen the other day when he asked Dean to dinner. It was obvious to Castiel that Gabriel did actually like the man. So the questions in his mind were what the hell had Dean Winchester done to his brother and how would he dispose of his body when he found out?

"So I take it we won't be seeing him again then." He ventured to say. One part of him hoped Gabriel would say that he was right. He didn't want his brother to have to see the man who had hurt him, but on the other hand, if he was to find out what had gone wrong, he really needed to see them interact with one another.

"Of course we will Cassie. He has a lesson the day after tomorrow." Gabriel replied as if he had no idea why Castiel would say such a thing making Castiel frown at him. In his experience, which yes was limited due to his previous career choice, when two people broke of a relationship they didn't tend to want to hang out with each other.

"He didn't cancel then?" He asked, to just make sure.

"Why would he? Dean and I agreed we were better off as friends." Gabriel replied with a shrug of his shoulders as if it was of no consequence making Castiel narrow his eyes once more.

"Right." was all he said in reply. He then took his coffee and left the office to go to the hanger and prepare angel for the flights he had that day, and to ruminate over all the different ways he could take his revenge on Dean Winchester for hurting his brother.

And Gabriel left in the office let out a sigh of relief. Well he had done his part and told Castiel that he and Dean were over and all was right, though by the look in his brother's eyes he wasn't sure he completely believed him, though he wasn't sure which part. I mean he knew he was a good actor, but surely he wasn't so good that Cassie had actually thought he ** _really_** liked Dean, was he? That would be just stupid. With a shake of his head he went back to the paper work in front of him. Looking down he realised that what he was looking at was for one of his different companies and he was hearty glad that Castiel hadn't come over to see what he was working on. Putting it away in his draw he turned to the books for the flight company and got to work on them instead, putting all thoughts of Dean out of his mind with ease.


	22. Chapter 22

**Hello my dears. I would like to thank Little Cinch for the lovely review.**

 **Here's another chapter for you. I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel had spent the days following his discovery that Gabriel and Dean had broken up watching his brother carefully. He had come to the conclusion that Gabriel was very good at hiding his hurt from him, though he understood that. If he had been in Gabriel's position he would have done the same thing, though he would probably be more belligerent, but that was just his personality. And so he had thought about how to get the truth from Dean rather than his brother. And as such had come up with the best plan ever. Dean's next lesson would be taking place in the air. Once Castiel had him in his control there was no way that Dean could lie to him. Thus the morning of Dean's lesson he came bounding in with a devious smile on his lips at the thought of scaring the shit out of Dean Winchester. Yes today was definitely going to be a good day.

* * *

Gabriel didn't think much of his brother's good mood. He put it down to the fact that today Castiel would be seeing Dean for the first time when he could actually flirt with him without the hindrance of him dating his brother. He had forgotten all about his suspicions that Castiel hadn't believed him, and he really didn't think Castiel would have any other reason for being in such a good mood. It fact it had been a while since he had seen his brother so happy when he wasn't flying. He was glad that everything seemed to be working out.

* * *

Sam arrived at Dean's garage ready to go with him for his lesson. Dean on the other hand had forgotten about his brother's offer and as such was rather surprised when he came out to his car to find his brother leaning against it.

"What are you doing here?" He asked confused, making Sam roll his eyes at him.

"I'm coming to your lesson remember? Help you sort out the mess you've gotten yourself into?" Sam replied as if talking to a child.

"Oh no need, Gabe and I have come up with a new plan." Dean replied a spring in his step that Sam hadn't seen before. He was extremely confused about why Dean would be so happy, especially as he was going to have a flying lesson, even if he did have the hots for his instructor.

"Do I even want to know?" He asked as he got into the passenger side of baby.

"I don't know do you?" Dean asked with a cheeky grin as he turned the key and the car came to life with 'Danger Zone' by Kenny Loggins screaming out of the speakers.

"You can tell me on the drive." Sam replied moving to turn down the stereo as Dean started to sing off key and pulled out of the garage.

And as they made their way to the airfield Dean did just that. Telling Sam all about the conversation he and Gabriel had had and the solution they had decided on. Sam couldn't quite believe how naive these two men seemed to be. Did they really think that Cas would make a move on his brothers ex? Or for that matter he wouldn't think the break up was all Deans fault? Because Sam knew, if he was in Cas' position he would definitely be blaming Dean. And thinking of ways to fix it all. That was what a younger brother did after all, they could be just as protective as there old counterparts, even if said counterparts never realised it. Oh well, he would see what the situation was when they got to the hanger.

* * *

Dean lead the way into the office smiling all the way, or at least he was until he turned to look at Cas, the first thing he always did when he arrived, and caught the predatory look on his face, and when he smiled at him it look to him like Cas was a big cat who had just seen a little mouse walk into his house. That look made his eyes widen in fear.

Sam who had followed him in followed his stare and guessed that that was Castiel. Hmm, he could see his brother's attraction, in an academic way, he wasn't the slightest bit gay. But the guy was attractive. When all his brother did was stare at the guy who stared right back he decided he needed to break the, whatever it was that was going on, and as such coughed, loudly. Of course this course of action gained not just the attention of the two who had been staring but a slight chuckle from none other than Gabriel Novak who had been sitting behind the desk and as such Sam hadn't spotted.

"Hi guys. Um, this is my brother Sam. Sam this is Cas and Gabe." Dean said into the room rubbing the back of his neck embarrassed by his behaviour and going red. Seemed he still hadn't been curled of blushing when he was caught staring at Cas.

At these words Castiel turned to the man with Dean and narrowed his eyes at him, he wondered why on earth Dean would bring his brother with him, unless he wanted lessons, though he didn't seem the type to Castiel. Then the thought came to him that maybe Dean had brought him for moral support. He was after all seeing his ex and his ex's brother, maybe he felt having someone on his side would be good. With that he inclined his head slightly in the taller man's direction not saying a word, making Gabriel rolled his eyes at his brother. He then stood from his desk making his way round and held out his hand.

"Hi Sam, pleasure to meet you." Gabriel said in a friendly tone and a genuine smile on his face. Dean had told him so much about his little brother he felt like he knew him already.

"Yes, um, Gabe. You too." Sam replied in a breathless tone as he hurried to grab his hand and shake it, making Gabriel to narrow his eyes at the younger Winchester. And then-

"Do I know you?" He asked causally as he looked up at him. He looked vaguely familiar. And then when Sam's eyes widened at his words he realised where he had seen this man before. And it was somewhere he didn't want Castiel to know about thank you very much.

"No doubt I've seen you around town at some point. Castiel why don't you take Dean for his lesson and Sam here can keep me company." He said smiling to the room though everyone there heard the tone of command underneath his words.

"Agreed." Castiel growled out and turned to the hanger, but not before he saw the two Winchester brothers exchange a look. That look puzzled him, and wondered once again why Dean would bring Sam here. Unless, maybe Dean didn't want to break up with Gabriel and Sam was here to persuade him to give Dean another chance? That was possible he supposed, after all his brother had been telling the truth that he agreed that he and Dean weren't suited for each other. Maybe Gabriel had been the one to break it off, but if that was the case, why would his brother do that? The only thing Castiel could think of on that brief walk to his angel was that Gabriel had thought that he wanted Dean and therefore didn't want to get in his way. If that was the case then Castiel had to get Dean and Gabriel back together, somehow. It looked like he would have quite a few questions for Dean once they were up in the air. The only thing to think of now was to wonder what maneuverers he would do if he didn't like the answers. A loop the loop sounded like fun to Castiel.


	23. Chapter 23

**Hello again. I would like to thank Little Cinch for the review.**

 **So last chapter of the day. Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

Once Dean and Castiel had left Gabriel gestured for Sam to sit down and offered him coffee which he accepted. Then Gabriel sat himself back behind his desk and looked over the man opposite him.

"So you're one of my lawyers." He said without preamble.

"I work for the firm that represents you Mr Novak. But I am only a junior there, at present." Sam replied very polite and correct, he suddenly realised that in coming here to sort out Dean's love life he was going to be spending the next hour walking a tightrope of a conversation with the one man who could make or break his career.

"So you have aspirations do you?" Gabriel asked over the rim of his own coffee. He did love to intimidate people on ocCasion.

"Doesn't everyone?" Sam replied in a steady voice. He would not show weakness to this man. This made Gabriel smile and drop the act as he relaxed back into his chair.

"I like to think so. So why you here Sam? And no more Mr Novak, call me Gabriel." He said with a wave of his hand at the younger man.

"Very well Gabriel. Dean told me of the… situation here and I wanted to see if there was any way I could help him out of It." Sam replied mincing Gabriel's relaxed pose.

That sentence made Gabriel throw back his head and laugh. Oh good luck with that one Sammy, he though. He and Dean had been trying to do just that the whole of their 'date'.

"I like you Sam. do me a favour though, don't tell Cassie who I am." Gabriel replied with a smile still on his lips for the younger Winchester.

"You haven't told him?" Sam asked with a frown on his face. How on earth had Castiel not discovered who Gabriel Novak was? It wasn't like he hid in the shadows, he was the face of his company as well as the brains.

"No. I don't want him thinking differently of me. I think you of all people could understand that. You are here after all to tell me to back off from your brother and leave him be, right?" Gabriel said still smiling at Sam who tensed once again. He really had to remember who it was he was talking to.

"I was, but now… I don't know what to think." He replied honestly to the man across from him. He had no idea what to make of Gabriel either.

"Well I think you think I've royally screwed up. Any suggestions how I can fix it Sammy?" Gabriel asked lightly, though in truth any help would be good in his mind. Gabriel after all hadn't missed the look Castiel had given Dean upon the Winchesters arrival, and that look did not bode well for his and Dean's plan.

"Please don't call me Sammy. Only Dean does that." Sam mumbled, then went red as he remembered who he was talking to.

"I know. He's told me a lot about you." Gabriel replied with a smirk at the younger man's blush.

"Oh god." Sam said wanting to sink into the floor right then and there. That or kill Dean, either would work right now.

"Ah, it's not that bad. At least your brother doesn't call you assbutt." Gabriel suggested raising his coffee as if in a toast to Sam.

At that Sam eased in this illustrious man's presence. He wasn't that bad, and he could see how Dean would call him a friend. He had none of the pretension that Sam had assumed he would have being Gabriel Novak, though he guessed, as a self-made man he was kind of down to earth. Even if Sam knew he had a killer streak in him if crossed. Though he had no intention of crossing him, so he should be fine, he hoped.

* * *

Dean followed Castiel to his plane, and when he got inside Dean followed. He had no idea what to say to the guy. He was supposed to be flirting with him and getting him to like him, but the look he had given him in the office scared Dean so friggin much he could barely form words. When Cas started the plane through Dean had other thoughts to occupy his mind. Namely how to get through a flight in this freakin' death trap without puking or passing out. With that he clutched his seat with both hands and gritted his teeth.

Castiel looked over at his passenger as he did a preflight check and briefly he felt sorry for the guy. He really didn't like flying. But Castiel pushed down his personal feelings as much as he could. He was here to get the truth out of Dean about what happened between him and Gabriel and fix it.

With the he turned the plane, taxied down the runway and pulled her up into the air. Once at a cruising altitude he turned to Dean who was white and shaking.

"You are going to be fine Dean." He said as gently as he could. Even if he wanted to scare the shit out of the guy even his heart couldn't take the petrified look on Dean's face. He almost turned the plane round and took her back down. Almost, he would get his answers first.

"Em-hm" Dean replied not opening his mouth worried about what would come out if he did.

"Dean trust me. I am not going to let anything happen to you. If nothing else I'm sure Gabriel would kill me if I did." he said nonchalantly pretending to be looking out the window, but in actual fact watching Dean very closely out of the corner of his eye. And At that Dean turned to him with a frown on his face making Castiel smile. Yes he had got Dean's attention now. "Well he likes you Dean, a lot." He continued.

At that Dean shook his head in a no, still not ready to speak.

"No? Why do you say that? Was he the one who finished it then?" Castiel asked casually, it really was easy getting answers this way. If only Gabriel was scared to fly. Or though he was sure he could perform some manoeuvres which would make even his brother blanch. Ah now there was a happy thought. But back to dean right now.

As an answer to that Dean short of shrugged his shoulders and waggled his head in what Castiel guess was a sort of 'we did it together' answer.

"You like him don't you?" he asked casually and Dean frowned again in thought before he nodded his head once. That was enough for Castiel. It was obvious to him that Dean like Gabriel and Gabriel liked Dean, all he needed to do now was get them back together. Though how he was going to do that he had no clue. He knew, if he was Gabriel he would be able to come up with some subtle plan, but subtlety had never really been his thing.

* * *

Dean didn't understand why Cas was asking him these questions and he wondered if it was a trap of some kind. But when Cas asked if he liked Gabriel he was really confused. Because he knew Gabe had told him they had spilt and that they were friends, so yeah sure he liked him. And so he nodded his head once. Hoping that was the right answer. Not that he was truly thinking right, he was up in the bloody sky. God how he hated this, and he wished briefly that Cas would interrogate him more, anything to take his mind off of where he was. With that he closed his eyes and leaned back against the seat and took deep breaths in through his nose. Cas had told him to trust him, and he did. He trusted Castiel. With that he felt himself relax as he thought about Cas, the sound of his voice and the feel of his touch. Concentrating on that he found that he could loosen his hold on the sit and his breathing returned to normal. As long as he keep thinking about his pilot and being in his hands, quite literally in some of his thoughts, he was okay. He. Was. Okay. That alone was a miracle in Dean's mind.


	24. Chapter 24

**Hello my angels. I would like to thank WarpedMinded, rainystv and Little Cinch for the wonderful reviews. I'm glad you like it.**

 **So here we are, another chapter. Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

Dean followed Cas back to the office once he had returned the plane to the hanger. He really wasn't thinking anything except how freaking glad he was to be back on the ground. He had been tempted to get on his knees and kiss it when he got out of the plane, but he couldn't do that in front of Cas. Especially as he was rather proud of himself. He had managed to get through the whole flight without puking his guts up or passing out once. He felt that really did deserve some sort of celebration. Maybe he would get a beer on the way home. As they entered the office they were greeted with outlandish laughter that came from two people. Turning they saw Sam and Gabriel sitting each side of the desk and they were both laughing heartily. When they saw them come in Sam gulped and went red before turning to his brother, and Gabriel just smirked up at the two, though his eyes were also drawn to Dean as his face was still as white as a sheet.

Castiel had watched both of their brother's responses when they arrived and he narrowed his eyes at his brother. It seemed that Gabriel had got along with Sam but the look he sent Dean was not one that said he was about to ask the elder Winchester out once more. And looking at Dean, Castiel realised that he could barely talk let alone ask his brother on a date. So that left it up to Castiel, very well. Turning to Dean he spoke.

"Dean, I was wondering if you wanted to go for a drink on Friday?" He asked in a no-nonsense voice making every eye in the room turn to him. Sam with surprise, Dean with hope, and Gabriel with a knowing look sparkling in the depths of his eyes. Not that Castiel noticed any of these except Gabriel's, looking at his brother he realised that Gabriel though that he was trying to ask Dean out on a date for himself. But before he could correct that assumption Dean managed to get a word out from between his lips.

"Yeah." He whispered nodding his head, though not as vigorously as he normally would have at the idea of going on a date with Cas. He still wasn't sure his breakfast would stay down if he did that.

"Excellent. You can pick Gabriel up at 6." And with that Castiel turned and marched out of the office back to the hanger to look after his angel after her flight. Leaving behind him three very stunned people.

* * *

Dean watched Cas leave then turned to Gabriel and just looked at him blinking his eyes as if to ask 'what the hell?'

"I have no idea… but, I'll sort this Dean-o, fear not." Gabriel replied to the unanswered question looking at the door Castiel had just left by. It looked like he was going to have to have a serious conversation with his brother about whatever stupid idea he had gotten into his head.

At that Dean nodded once more then turned to Sam who could read his eyes with ease.

"I think we should go. It was nice meeting you Gabriel." Sam said turning to the man who was frowning at the door to the hanger.

"Yeah, you too Sammy. You too." Gabriel replied not that he was truly paying attention to them anymore, he was trying to think of what he was going to say to Castiel.

With that Dean and Sam left, Sam taking the keys from Dean so he could drive them back to the garage. He had no idea what was going on now, but he thought that if Gabriel said he would sort it, he would. Gabriel was not someone who didn't manage to do what it was he set his mind to doing. He turned to his brother thinking that he should say this or something similar, but looking at his still pale face he thought it would probably be best to leave Dean to his thoughts.

Dean on the other hand was trying to work out what had just happened. Because it seemed to him that Cas had just arranged a date between him and Gabriel. But why in the hell would the man do that? I mean seriously, where did he get the idea that he and Gabriel had any feelings for each other what so ever? But it was all too much for Dean right then. He just wanted to lie down and close his eyes and forget the whole horrible morning.

* * *

Castiel was fiddling with something in the engine of the plane when Gabriel stormed in and turned off the radio with as much anger as he could generate. Turning to him with a raised eyebrow Castiel crossed his arms and leaned back against his plane. He had a feeling his brother would act like this after his stunt of getting him and Dean back together, but he didn't care. He could weather the anger of Gabriel Novak. Especially when he knew that what he had done was for his brother's happiness.

"What did you think you were doing?" Gabriel asked in a low controlled voice.

"What you and Dean were too pig-headed to do." Castiel replied with a smirk.

"Excuse me? Dean and I split. And we were happy with that." Gabriel answered anger starting to lace his tone as he stared at his brother.

"No you weren't. I know you weren't." Castiel denied vehemently to him.

"You know nothing about me Castiel." Gabriel replied in a low, deadly voice.

"Really? I'm your brother Gabriel, I think I know enough." Castiel answered smugly.

"What? Do you really think I like Dean?" his brother replied in an oh so innocent voice.

"Yes." Castiel nodded. He really, really did believe his brother liked Dean, and he was prepared to let any feelings he had for the man go in returned for Gabriel's happiness.

At that Gabriel shook his head and looked upwards as if praying for guidance, he couldn't believe that his brother had fallen for his act hook, line and sinker. It seemed 15 years apart and neither of them knew the other anymore. Briefly he sighed at that thought. He was going to have to get to know this new Cassie, but first things first.

"I'm not gay Castiel." He said in a completely serious voice making Castiel question, for the first time, that which he had thought was truth. With a frown for his brother he remembered all the conversations they had had about Dean.

"But… you dated him, you said that was the exception." He said as if that was proof enough of his belief in Gabriel and Dean.

"For god's sake, he's hot, I'm not denying that. But I don't swing that way. Never have, never will. Dating Dean was a moment of insanity that I returned from the other evening. I like him, as a friend Castiel. Nothing more." Gabriel stated hoping that it would get through his brothers head.

"Oh." Castiel replied eyes wide at what he had done. Did Dean know this? If so why did he agree to go on the date?

"Yes, oh. Now you had better find a way to fix this. Because if we lose Dean's custom I'm through with this business and with you." Gabriel replied with a snap of command in his voice.

"And how am I supposed to fix it Gabriel? It's you he likes you assbutt." Castiel growled at his brother. He had had enough of him treating him like a lieutenant.

"Oh come on. You're the one he flirts with. You date him." And with that Gabriel stormed out of the hanger a smile forming on his lips as he thought that went rather well. He may not be as he planned it, but at least now it would get Cas and Dean on a date, what happened from there would be up to them.

And Castiel stood there with his mouth open at what Gabriel had suggested. Not because of the words his brother had spoken but his reaction to them. Because when Gabriel had suggested he date Dean his heart had leaped and his mind screamed in joy at the idea. And he suddenly, blindingly, came to the realisation that he liked Dean, and he liked him a lot. What the hell was he supposed to do now? Taking a deep breath he turned back to his angel and breathed out evenly, it was Wednesday, he had two days to come up with some solution to this problem, and maybe he should take Gabriel's advice. Maybe he should be the one to go on the date with Dean. But the question was, would Dean want to go on a date with him?


	25. Chapter 25

**Hello my honeys. I would like to thank Willow580 for the lovely review. I would also like to thank all you lovely people who have followed and favoured since my last update.**

 **So here is the next chapter, I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

It was Thursday afternoon and Castiel had decided that what he needed to do was inform Dean of his mistake and that Gabriel wouldn't be going on a date with him. And then maybe he could persuade the guy to go out with him instead.

But he had yet to pick up the phone to call him.

He just wasn't sure what he would say. Getting into his car, a frown on his face he turned the key to hear a strange stuttering sound coming from the engine. Now normally he would drive over to the hanger and fix it himself, cars aren't that much different to planes after all. But this time he didn't. He sat there thinking. Because he happened to know a mechanic, and said mechanic also just happened to be the person he most wanted to talk to right now. With that in his head and the thought that it would probably be better if he spoke to Dean in person he drove his car slowly to Winchesters auto-repair shop.

* * *

Dean was working in the garage that afternoon when he heard a sick car approach. Walking outside he found himself staring at the car as it pulled into the parking lot. It was a car he had seen regularly at the air field. His eyes moved from its hood to its driver as it pulled to a stop only for his stare to meet the blue eyes of Castiel. Now Dean had had a call from Gabriel yesterday informing of what he had told his brother and as such Dean had been waiting impatiently for the call from Cas asking him if he wanted to go for a drink with him instead. It still hadn't come. But now, here in his garage was the guy himself. Maybe Dean could get the conversation on to the idea of them going on a date while he looked over the car. With that in mind he approached Cas with a massive smile on his face.

* * *

The first person Castiel saw as he brought the car into the parking lot of the garage was Dean and he let out a sigh of relief. It had crossed his mind on the drive over that maybe Dean wouldn't be there today, but there he was. His overalls tied around his waist and a tight black tee which accentuated his chest, making Castiel almost forget why he was there. And then he smiled. Dean smiled and it seemed as if the world became that much brighter. And Castiel was seriously getting worried with himself. He was either falling hard for this guy, or going completely nuts. He wasn't sure which he would prefer he thought, when he realised that Dean still thought he was going on a date with Gabriel the next evening. That was probably what the smile was about. That he was glad that he, Castiel, had got him back with his brother. Great, bloody fan-freaking-tastic. Castiel was about to break the heart of the guy he really liked. There was no way Dean would date him after he did that.

"How can I help?" Dean asked as soon as Cas was out of the car. He had made his way round to the driver's side and was now standing close to the other man, probably too close, but neither of them noticed.

"My cars making a funny noise." Castiel replied staring into those luscious green eyes. Of course as soon as the words were out of his mouth he could have smacked himself. How in the hell could he sound so freaking idiotic?

"I noticed." Dean replied humour lacing his tone at Cas' words. Not that he moved to take a look at the engine or anything, his eyes were busy staring at Cas right now.

"I was hoping you could fix it." Castiel continued staring at Dean. He was so close he could easily close the distance and place his lips on Deans. No, he had to do this right. With that thought Castiel moved away from Dean and moved his eyes to his car.

"Sure, pop the hood." Dean replied turning his eyes to the car when Cas did. He wasn't sure what else to say. He had noticed when Cas had moved just how close they had been standing.

With that Castiel did as Dean had asked and when the mechanic bent over the engine Castiel couldn't stop his eyes from traveling to his ass. It was so fine. With a shake of his head he moved so he was leaning back against the car next to Dean and rested his hands behind him.

"So what do you think?" He asked after Dean had had a while to look.

Dean meanwhile had been thinking about a lot of things. Not one of them had anything to do with the car in front of him of course, they had everything to do with the guy standing next to him though. Damn did he have to smell so good? And those hands were sculptured perfection.

"Umm, looks like the spark plugs need replacing." Dean finally replied pulling himself out from under the hood. And wiping his hands on a rag from his pocket.

"Can you do that now?" Castiel asked, he hoped Dean said yes, then he would have time to talk to the guy, explain everything. And ask him out. Though now he had seen him he really wasn't sure he could do it. Break Dean's heart.

"Sure. Bring it in." Dean replied gesturing to the garage and when Cas went and got back into the car Dean let out a deep breath. He had to work out how to get this conversation onto the possibility of them.

* * *

Castiel went and got back into his car and drove where Dean had pointed. Looking round he saw that they were the only ones in the place. That was good, he didn't want to have the conversation they needed to have with an audience. Though when he got out of his car all thoughts of telling Dean about his mistake with him and Gabriel went out the window as he heard Danger Zone playing on the radio.

"Good song." He said smiling at Dean.

"Yeah, one of the best." Dean replied. And that was it, Dean and Castiel fell into an easy conversation about decent music and radio stations, which quickly led into a one about concerts and from there stories of their lives. In fact they talked and laughed none stop while Dean fixed the car.

Before either of them knew it the car was fixed and neither of them had said anything of consequence to the other. As he was paying Castiel opened his mouth to speak, but seeing the hope in Dean's eyes he shut it and thanked him before leaving.

Leaving Dean still believing he was going on a date with Gabriel the following evening.

And Dean, well he watched Cas drive off in his car with a sense of depression. Castiel hadn't asked him out, or said anything about the next evening. With a sigh he closed up the garage. He had though that Cas liked him as well. Hell, even Gabriel had thought that. They couldn't be both wrong, could they?

* * *

That night Castiel found himself in that British bar once more, he had been walking and found himself outside The Roadhouse, but he wouldn't go in there, he might see Dean. So instead he had come here. He sat down heavily on a stool and once more ordered a Glencraig whiskey, only for that British voice to speak again.

"Back again, are we kitten?" Crowley asked with a smirk from what looked like his permeant position at the bar. He was once again wearing that black suit and red tie. What was it with this guy?

"Yes." Castiel snapped at him. He did not want to share pleasantries or even thinly vailed threats right now thank you very much.

"Why this time?" Crowley asked in a friendly voice turning on his stool so he was facing Castiel and gesturing to the bar man to leave them the bottle.

"Because I screwed up." Castiel replied draining his glass only to have Crowley refill it once more. Even if he did shake his head at Castiel's treatment of the whiskey.

"Tell me about it." Crowley said in that honeyed voice of his. He was happy to listen to Castiel's problems all night if needs be. It gave him something to do after all.

And so Castiel did just that. He told Crowley everything that had happened starting with Dean's arrival in the office up to how he had left him at the garage that afternoon. And Crowley, being the highly perceptive person he was, was pretty sure that Castiel's brother had been playing him. Trying to get him with Dean. But he won't out the plan, listening to the boy beside him he understood why his brother had done it. He did need someone in his life, and this Dean sounded like just the thing. Therefore at the end of Castiel's tale he had only one piece of advice.

"Well your solution is clear kitten. Don't tell him. Make up some excuse as to why your brother can't make the date and invite yourself along instead. Then persuade him that it's you he wants not your brother." Crowley said as if it was obvious. He then placed a stack of bills on the bar and with a wave walked stately out of the door, leaving Castiel looking into his half empty glass as he thought over his words. Draining it as he came to a decision.

That plan was low and conniving… but it could also work.


	26. Chapter 26

**Hello my angels. I would like to thank purple (Guest), Little Cinch and rainystv for the wonderful reviews. I would also like to thank all of you who have followed and favoured since my last update, you're all awesome.**

 **So here we are the next chapter, I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Friday afternoon and Gabriel swiftly left the office at 5.30. He had had a desperate call from Dean saying that Castiel had yet to contact him and so he had told him to just get his ass here for six. And Gabriel did not want to be around when he arrived, well actually he would love to see what was going to happen, but he thought it was probably better if he split and left it to the two men who actually liked each other to sort out asking the other out. And so with a casual wave and a grin he said goodbye to Castiel and walked out the door, ready to start a nice relaxing weekend with his girlfriend.

Castiel had put on an air of causal relaxation for Gabriel all day and made sure he kept it up as his brother left. Of course as soon as Gabriel had left the building that mask fell and the panic started to set in. he couldn't believe he had taken advice from that damn Crowley again. It hadn't gone so well last time had it? In fact Crowley's last advice had brought him to his current situation. But it was too late now to change his mind, instead he would do the sensible thing and change his shirt instead. He had brought with him his best blue shirt which matched his eyes and so went to the bathroom and put in on. He then looked at his hair wondering if he should try to do anything with it, but decided against it. He didn't want to look too much like he was trying to get Dean to date him. With a nod he then went out and sat behind Gabriel's desk so he could pretend to be doing some work when Dean came in. of course for the next 25 minutes all he did was lean back and stare at the ceiling seeing a pair of gorgeous green eyes and dirty blonde hair. And an awesome chest encased in a tight black tee.

* * *

Dean pulled up in the parking lot of the airfield with a sigh. He had no idea why he was here or what was going to happen. When Gabriel had told him to come here as if he still thought they were going on a date he had almost refused. Hell he had almost not come without telling either of the Novak's, that would teach him. In fact his mind had been going backwards and forwards over the idea of not coming, to the idea that he may just get to spend the night with Cas and wasn't that worth one more lie? All day. But in the end the idea of seeing Cas won out and so he had gone home, showered and put on a shirt so he looked like he was planning on going on a date. With another sigh he got out of his car and made his way to the office. He hoped this would work out.

* * *

Castiel was still leaning back in the chair when he heard the handle of the door turn. Quickly sitting upright he grabbed the papers in front of him so it looked like he was actually doing something other than waiting for Dean.

"Hey Gabe." Dean said when he saw someone behind the desk. He didn't take much notice of who it was, instead he was looking round for Cas. He was going to be here right?

"Sorry Dean, I'm not Gabriel." Castiel replied putting down the papers he hadn't been reading, or even seeing in all honesty.

At the sound of Cas' gravelly voice Deans head swung round to him, to see him looked completely divine in a blue shirt. God he was gorgeous.

"You're not." Dean answered and almost hit himself with the inanity of it. Why couldn't he ever say anything clever and funny when he was talking to Cas?

"Yes, sorry, umm, Gabriel asked me to tell you that he can't make your date this evening and he's sorry." Castiel mumbled as he rearranged the papers not looking at Dean as he lied to him.

"Oh." Dean responded, but before he could think of anything else to say Castiel continued.

"Yes it was some emergency at home. So… he's sorry." At that Castiel finally looked up at Dean and his eyes were caught with the other man's green one.

Dean listened to Castiel stubble out his excuse and smiled. First rule of lying, you never give too much information unless asked for it. With that smile he relaxed. Cas, for all his cocky self-assurance was really bad at lying. He liked that.

"That's okay. I'll leave you to your work then." Dean replied not moving as he stared into Castiel's eyes.

"I was just about to leave myself." Castiel replied with his sassy smile returning to his face. Dean didn't seem too upset by his brother not being here. Therefore Castiel reverted to his true self. Enough with the self-effacing crap.

"Really? You got plans this evening?" Dean asked as casually as he could manage.

"None at present." Castiel replied with the raise of an eyebrow and a hint of warmth in his eyes.

"You want to come have a drink with me?" Dean asked as if the idea had just popped into his head and he hadn't been wanting to ask that question since he met the guy.

"Yes Dean, I would." Castiel replied with a smile, though he knew Dean was only asking him because they had become friends of a sort and Gabriel was not here. But maybe he could get the other man to transfer his feelings to him. It would be his challenge for the evening.

"Great." Dean said with the widest smile possible. Yes, he and Cas were finally going on a date. Well he hoped it was a date at any rate. Hell, he would make it a date. By the end of this evening he was going to kiss Cas, he would make sure of it.

* * *

Dean drove his car to his home and dropped it off before he and Cas walked to The Roadhouse. He was going to be drinking a lot tonight so best not to have his car with him. His plan was to get Cas smashed so that they could admit their feelings for each other and finally get it together. He just hoped that plan worked, though as he could drink most people under the table, he wasn't concerned that he would be the drunken idiot at the end of the evening.

He really should have been.


	27. Chapter 27

**Hello again my darlings. Now what can I say about this chapter? I'm mean and horrible, please don't hate me?**

 **Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

The evening all started out innocent enough, Dean and Cas entered The Roadhouse and sat at one of the booths before ordering drinks. It was the order that was Dean's downfall. He decided that they should have whiskey chasers with their beer, it would get Cas nice and drunk, get him to loosen up a bit. What Dean hadn't factored into this plan was that Cas was ex-air force, and as such could drink for his country if needs be. Two hours into this drinking session, after Dean and Cas had had many an interesting conversation about… nothing, music, brothers, work and more nothing, Dean was starting to realise his mistake. He was really rather drunk and yet Cas still seemed fine. Damn that wasn't the plan.

Castiel on the other hand was having a great time talking with Dean and drinking, he found it rather entertaining that Dean was getting so drunk, though he wasn't so amused when they had been talking about Gabriel, he was sure Deans voice went softer when he said his brother's name. But apart from that, it seemed to be going well. He would succeed in his challenge to get Dean to like him.

* * *

Another hour later and Castiel decided that Dean should probably leave now, he was rather inebriated, and if truth be told Castiel wasn't exactly sober. So grabbing the other man's hand he pulled him up and led him outside, not letting go.

Dean of course was happy to follow Cas anywhere, so didn't complain when they left. In fact it would work really well with his plan. With that in mind he grabbed Cas' hand and pulled him back with him into the alley that ran next to The Roadhouse. Once there he pulled again so Cas was in his arms, he then lowered his head and gently kissed the other man's lips. He didn't want to force Cas if the guy wasn't interested, Dean just really hoped he was.

And oh was Castiel ever interested. His whole body sang when he felt Dean's lips on his. But when the kiss remained light and gentle he growled. He wanted more. With that thought he turned Dean so he was now pressed against the wall of the bar and threading one hand through Deans hair and the other grabbing his ass, he kissed him with all the pent up passion he had been unaware he had.

And Dean let him. Oh man it was heaven, Dean just did his best to keep up with the other man, one hand pressed against Cas' solid chest and the other cupping his head. It was perfection in Dean Winchesters mind, and so much more than fantasy ever could be.

Finally Castiel pulled back from the kiss to catch his breath, though he didn't remove his hands.

"Come back here Cas." Dean whined grabbing his shirt and trying to pull the man back to him. He never wanted to stop kissing Castiel.

At that Castiel smirked, he liked hearing Dean beg, but, "No, we can't do this. You are drunk." He said instead.

"Doesn't mean I don't want you. Hell I've wanted you since the moment I set eyes on you." Dean answered still in the begging tone, but now with a hint of the sensual.

This made Castiel stop and frown, because that wasn't true? Was it?

"And what about my brother?" he asked Dean taking care to make sure his voice sounded light as if the answer was of no consequence to him.

"Gabe and me? That was all a fake, I mean come on Gabe is as straight as an arrow, plus he's got like a really hot girlfriend." Dean replied in the same casual tone, not realising what he had just said until Castiel stepped away from him with narrowed eyes.

"What do you mean?" Castiel asked in an even but low tone which, had Dean been soberer, would have had him on high alert, but he wasn't, what he was, was heartily sick of all the lies. Or at least some of them.

"Gabe's girlfriend is hot. I've seen the pictures, I mean who hasn't right?" Dean replied with a shrug.

"What are you talking about Dean?" Castiel asked again in the same tone as before.

"Google your brother, then you'll know everything. But later, now come here and kiss me." Dean replied trying to pull Castiel to him once more only to have the other man take another step back so he couldn't reach him without moving away from the wall.

"Why were you pretending to date Gabriel?" Castiel asked next. It seemed drunk Dean was far more honest than the sober version of the man. As such Castiel was going to get everything he could from the man.

"Cos he wanted to get us together and thought we should make you jealous or some shit like that. I don't really know." Dean replied then watched as Castiel turned away from him. "Hey were you going?" He asked in a desperate tone. Cas couldn't leave him, they had just got together god damn it.

"To talk to Gabriel. I would advise you drink some water before bed." Castiel replied over his shoulder as he continued to walk away.

"Don't leave, I really like you." Dean begged, this could not be happening.

"You have a funny way of showing it Dean Winchester, what with lying to me and tricking me. Goodbye." Castiel replied turning to look at him with such a look of disgust on his face that Dean couldn't think of anything else to say.

And once Cas had left the alley Dean slammed his head back against the wall.

"Son of a bitch." He growled out to the empty air. Now what the hell was he supposed to do?

* * *

Castiel reached the end of the road in his righteous fury until he realised one startling fact. He had no idea where his brother lived. How in the hell could he not know where Gabriel lived? With a shake of his head he changed his direction and started walking to the airfield and their office. If there was one thing he did know it was that legally they had to keep copies of all employee's personal details, including home addresses. As such he could get Gabriel's from the office and then go and see what the hell this was all about, and get his brother to explain just what it was that Dean was implying.


	28. Chapter 28

**Hello my honey buns. I would like to thank Little Cinch and rainystv for the lovely reviews. I would also like to thank those of you who followed and favoured since my last update. You'll all awesome.**

 **So here's the next chapter, I know its short but it seemed the right place to split what I had written.**

 **Anyway I hope you enjoy it.**

 **Disclaimer: I don't own Supernatural.**

* * *

After a couple of tries Castiel managed to get his key into the lock of the office door. The fact it took him more than one go told him he was rather more drunk than he had thought, and a small voice in the back of his head ask if maybe he should leave this until the morning when he was sober. But Castiel was drunk, and as such was not going to be listening to any annoying sensible voices thank you very much.

Stumbling his way across the darkened room as he had forgotten to put the light on, he managed to get to Gabriel desk and turn on the table top light. With that on he sat down in his brother's chair and leaned back staring up at the ceiling. He couldn't believe that only a few hours ago he sat here wondering if he could get Dean to like him instead of Gabriel. But it had all been a lie. Dean had always liked him and his brother had taken him from him with some shit ass story about trying to make him jealous. The bastard that Gabriel was, he was a complete and utter… assbutt.

With that Castiel pulled himself up so he staring at the desk trying to think where Gabriel was most likely to keep the personal files. With a shrug he decided to start with the draws in the desk. Leaning forwards he pulled open the top one only to find boring paper work, he was about to close the draw when the name of the company involved caught his eye and made him frown. Because it wasn't the company he and his brother ran. Just what was Gabriel up to? With that he pulled out the papers to try and find out as much as he could about this other company. And hell did he find out a lot. It seemed theses papers were some sort of financial document, and the money they were talking about was enough to make Castiel's eyes to water. It was then he read the bottom of page, the bit that requested the signature of the CEO, the signature of Gabriel Novak.

What the freaking hell?

Castiel just stared at this bit of paper that told him his brother was CEO of a major company. Because there was no way that was true. I mean Gabriel didn't do anything but the paper work for here. Though thinking about it, there seemed to be an awful lot, more that Castiel would have supposed for their small business, so what-?

With that Castiel's eyes saw the computer on Gabriel's desk. He had originally planned to go and ask Gabriel about what Dean had said, but now one phase that sexy traitor had said rang in his head. Google your brother. What would he find if he put Gabriel Novak into the search engine? And why did Dean think he should do it? Castiel's eyes flipped from the blank computer screen to the papers in his hand until he sighed and placed the papers on the desk as he turned the computer on.

Once it was on he opened up the search engine and typed in Gabriel Novak. He was not prepared for what came up. There wasn't just a couple of companies and a Facebook page as he had dreaded there would be. No there was a whole freaking website dedicated to his portfolio. There were photos by the hundreds of him and some dark haired woman who was apparently his long term girlfriend. And there were a list of companies that listed him as a major member of the board. A massive list. It seemed his brother hand his fingers in many different pies. And all of them were very lucrative, hell he was even on the list of the hundred richest bachelors, even if he did have a girlfriend, one who it seemed was just as powerful and driven as Gabriel.

Castiel couldn't believe that this was his brother. Even if it was Gabriel in the pictures he just couldn't see it. Yes he knew his brother had a ruthless streak and could accomplish anything if he put his mind to it. It was just the Gabriel he remembered never did. He got top grades at school without any real effort, and got a scholarship to some Ivy League college just as easily. But Castiel had never thought what his brother had done with that first class education. When Gabriel had graduated Castiel was off in the air-force after all. Receiving the occasional letter from Gabriel at holidays but that was about it. They rarely spoke in the last 15 years. But why hadn't his brother told him? If not then, then now that he was back? Why was his brother keeping this from him? Was Gabriel embarrassed about him? Or was there some other reason? Castiel also realised that Gabriel did not need to start the business with him, hell he could have just brought Castiel a plane and employed him as his pilot for Christ sake, so why?

With a shake of his head and turning from the computer he had a look around the office with dazed eyes. He finally settled on the filing cabinet. There was no point asking himself these questions in the dark of the office. What he needed to do was go and ask Gabriel, after he had ripped into him about Dean.

With that he went over to the cabinet and pulled the top draw open with force, pulling out files and throwing the ones he didn't want on the floor. Gabriel could sort it out when he came in on Monday, it would serve him right. Finally after going through two out of the three draws he found what he was looking for. The home address of Gabriel Novak.


	29. Chapter 29

**Hello again my dears. I would like to thank Little Cinch for the review. I would also like to thank those of you who have followed and favoured since my last update.**

 **So here we are, time to see how it goes with Gabriel and Castiel, enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

Reaching the coordinates of the address he had found for his brother Castiel sneered at the large electronic fence and gate. He betted his brother had cameras everywhere as well. Good they would capture their 'talk'. With that he ran at the fence and threw himself up as far as he could. He then pulled himself to the top and flipped over and landed on the other side in a crouch. A smile on his lips, he hadn't done that in a while after all, he stood and brushed himself down before sauntering across the grass making sure he keep an eye out for any security guards his brother might have. He didn't see any, which was good, he would prefer not to have to knock them out just because Gabriel had pissed him off. It wouldn't really be fair to them after all.

Making his way to the big white double doors he raised his eyebrows. Damn theses doors where nearly larger than his kitchen. With a shake of his head to remove the thought he considered the bell, but then decided to go for the more physically satisfying solution and banged his fist against the wood. He repeated this until he heard a yell of "I'm coming." from inside. Satisfied that he would soon be getting answers he stood back and crossed his arms.

"Hello Gabriel." He said when his brother, who had obviously just got out of bed, opened the door.

"Cassie, what are you doing here?" Gabriel asked, his brothers voice waking like nothing else could. What the hell was going on?

"Good question." Castiel replied and then he pulled back his arm and punched Gabriel square on the jaw, making his brother swear blue murder as he rubbed the place his blow had landed, before Gabriel turned back to him to see that Castiel had once again crossed his arms and was glaring at him.

"Yeah, I probably deserved that." Gabriel finally said in a conversational tone.

"Probably? Definitely you assbutt." Castiel growled at him. Probably my ass.

"Yeah, okay your right. Though I have to ask. What **exactly** that was for?" Gabriel asked trying to work out exactly what it was his brother punching him for. After all there was a bit of list he guessed.

"Why is there more than one reason I would punch you?" Castiel asked trying for an innocence which didn't fool Gabriel for a second.

"Probably." He replied in a clam voice as he crossed his arms and leant against the doorframe, time to have this out then he guessed.

"Definitely." Castiel growled narrowing his eyes at his brother's Casual attitude. If Gabriel wasn't careful he would be meeting Castiel's fist again, and soon.

"So you going to punch me again, or do you want to come in and talk?" Gabriel asked in a friendly tone moving so Castiel could just walk in if he wished.

"I want answers Gabriel, and I want them now." Castiel snapped. He was not going to be schmoozed into being nice to his brother, no way, not tonight.

"Then ask the questions Cassie." Gabriel said with a sigh. How was he supposed to tell his brother anything unless he knew what it was he wanted to know?

"Why didn't you tell me the truth of who you are?" Castiel asked trying to keep himself as calm as his brother was. He could do this without going into a rage. It would be fine.

"I'm your big brother. That's the truth." Gabriel replied without blinking an eye. His brother was playing his game now, and he would win.

"You are also a millionaire who has a list of companies a mile long." Castiel snarled at him, though all Gabriel did was shrug as he answered.

"That's not who I am Castiel, that's what I do. And I damn good at it, hence the money."

"So why didn't you tell me that?" Castiel asked when he realised that actually his brother might have a point with that, damn him.

"I wanted to Cassie, I really did. I wanted to buy you a plane and set you up in your own place, but would you have taken that from me? Hell if I had told you the truth would you even have agreed to go into the business with me?" Gabriel asked in return. He had reasons for everything he had done, and almost all of them were right, **almost** all of them.

"I don't need charity." Castiel growled at the suggestion of his brother putting him up and give him a plane making Gabriel roll his eyes at his stupidity.

"It's not charity Castiel. It's my way of helping my brother." He answered starting to let his exasperation with this conversation show.

"And Dean, was that your way of helping to?" Castiel asked glaring for all he was worth. Because if he was truthful that was what hurt the most. It wasn't the secrets his brother had kept about what he did or how much money he had, those Castiel knew he could and would understand after he calmed down a bit. But what Gabriel did with Dean was inexcusable in his mind. He played with Castiel's feelings as if he was a puppet on a freaking string.

"What do you know?" Gabriel asked warily, for they were now approaching the one thing that in retrospect Gabriel was not so proud of. And he had no reasonable excuse for. Not one that Castiel would accept, hell Gabriel wasn't sure he accepted it anymore and it was his excuse.

"That you dating Dean was all a lie." Castiel stated in a steady voice after taking a deep breath. If he wanted answers from Gabriel he would need to stay calm.

"It was." Gabriel replied. With a nod. He wasn't going to lie about it anymore.

"Why?" Castiel asked and though he tried to hide it Gabriel heard the hurt in his voice. Oh god what the hell had he done to his little brother?

"I thought if you saw him with me you would realise how you felt about him and not just use him for a night's entertainment." Gabriel finally replied with honesty. He really wanted Castiel to understand his reasoning, even of it was seriously flawed.

"What the hell are you talking about Gabriel?" Castiel snapped. I mean why on earth would Gabriel think he would use Dean for just a night? If nothing else he was teaching the guy to fly, he would be seeing him on a weekly frigging basis. Not exactly one night stand material.

"I'm talking about you Cassie. I have set you up with loads of nice guys, and yet every one of them you used for sex and nothing more. You need someone Cassie, someone who will show you you aren't alone." Gabriel snapped back. Two could play this game, and when Gabriel found himself in the wrong he always defended himself that much more. It was the way he was. Sorry was not a word he uttered.

"I'm fine as I am Gabriel." Castiel replied anger starting to once again course through him.

"No Castiel, you're not. But fine. I give up. If you can't see the writing on the wall I'm certainly not going to spell it out for you. Anymore questions?" Gabriel growled in his low controlled tone which would send most people running, but Castiel was not most people. And as such he stood his ground, though he wouldn't argue with his brother anymore. But he would walk away with his head held high thank you very much.

"No." he replied firmly as his fists clenched out of sight.

At his response Gabriel closed his eyes and took a deep breath. He couldn't treat his brother like one of his errand employees. He was his brother. Breathing out slowly he opened his eyes and spoke again in a calmer, friendlier voice.

"Then do you want to come in and met my better half? We've got a spare room or 12 if you want to stay the night."

"No. goodbye Gabriel." Castiel replied and with that he turned and walked off down Gabriel's drive.

"Cassie, where are you going? Castiel." Gabriel yelled after him. It was like one in the morning, what was his brother thinking? He lived the other side of town and it wasn't like there were many taxi's in this area.

But Castiel ignored him and continued walking. Leaving his brother behind him screaming his name. Once he got back to the fence he climbed back over it and made his way back to his small shitty one bed apartment, stopping only to buy a bottle of the strongest liquor the 24 hours off-licence had.

He was going to get shit-faced and forget all about his brother and all about Dean. He just couldn't deal with this crap anymore tonight.


	30. Chapter 30

**Hello my darlings. I would like to thank Tie-Dyed Broadway and Little Cinch for the lovely reviews.**

 **So here's the next chapter, I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel woke the next morning feeling like someone was drilling into his brain. Moving slightly in his bed he screwed his closed eyes up tight as the midmorning sunlight shone through his eyelids from the uncovered window. It seemed he had forgotten to close the curtains before he passed out. Reaching out with his hand in what he hoped was the general direction of his bedside table he finally found what he was looking for by touch. Picking up the glass of water he took a sip, hoping that it would help remove the fuzzy feeling from his tongue and mouth as well as the residual taste of bad liquor.

Once his thirst was quenched he leaded back against his pillow, he was just about to drift off once more into beautiful oblivion when his phone bleeped. He groaned, but he knew that if he didn't look to see what it was, the bleeping about it wouldn't freaking stop. Reaching for it he cautiously opened his eyes to squint at the screen. He saw he had 5 missed calls and 2 voice mail messages. All from the same number. Gabriel. He was tempted to throw the thing across the room and smash it to bits so his brother couldn't contact him. But he knew if he did that Gabriel would just come over, for unlike him, his older brother knew exactly where he lived. And where the space key was kept.

With a growl, and the phone about an inch from his eyes he opened the messenger and sent a text to Gabriel that consisted of two words. Two words that he felt pretty up summed up exactly how he was feeling right then. With that done, he turned off his phone and rolled over going back to sleep without a care or thought. He was to hungover to give a shit about anything right now.

Gabriel on the other hand was sitting at his kitchen table, pancakes in one hand and papers from one of his numerous companies in the other, when his phoned bleeped informing he had a new message. Putting down the papers and putting the pancakes in his mouth he picked it up to see it was from Castiel. He was unsure about what it would say, whether it would be rude or slightly less so. Gabriel was under no illusion that it would be friendly. It was going to take his brother a while before he calmed down about this one.

So taking a deep breath and preparing himself to read a rant he opened the message to be greeted with only two words.

 _I resign_

That was it. That was all Castiel had to say about everything. Closing his eyes Gabriel wondered what he could do. It wasn't like he could force his brother to come to work, though Cassie would need money soon. And Gabriel knew he wouldn't ask him for it. He wished he could just text back that he didn't accept it, but that wouldn't work. Castiel would kill him if he did that. Gabriel needed a solution to make sure that his brother didn't fall into debt or worse, but first he needed to reply to Castiel text. Taking a deep breath he did just that.

And when Castiel woke next feeling a bit more ready to face the world and turned his phone back on he found just one message from Gabriel.

 _Very well, if that's what you want. But while you can resign from the business, you can't resign from family Castiel._

And Castiel had to text back to that. He could not let his brother have the last word on this one. No way in hell. Gabriel was the one in the frigging wrong, not Castiel. His brother was going to have to deal with the consequences of his actions this time.

 _Just watch me._

With that he pulled himself up out of his bed and made his way to his computer. He had some friends he needed to email. See before Gabriel had suggested the business one of Castiel's former colleagues had offered to put in a good word for him with his boss at a company which specialised in flying the rich and privileged around the world. It had not been Castiel's first choice of work, hell it wasn't even his second, being polite was never one of his best skills. But right now the idea of getting out of this hellhole and into the air appealed very much to Castiel Novak.

Hell he would willing be an airhostess and grovel to whoever needed it right now if it did that job. Anything to get away from Gabriel and Dean and all shit that had landed on his head last evening.

And Gabriel reading his brothers reply put his head in his hands. He had no idea how to make this better. He would do anything to get his brother back again, anything. But he could come up with nothing. With a sigh he pulled himself up out of his chair. He had things he needed to do now. Calls he needed to make to let the clients of Heavenly Wings Flight Training Company that there lessons would be cancel for the foreseeable future. God he had really screwed the pooch on this one. With a sigh he grabbed his jacket and went and got into his bright yellow Lamborghini. No need to use the beat up old car to go to the air field any more. He could travel in the style he liked to drive in now. No one to lie to anymore about what he had made of himself.

* * *

Once Gabriel got to the office he found the disarray of paperwork that Castiel had left strewn across the floor last evening. With a shake of his head he bent down and sorted it all out, putting it back in its proper place before he sat at his desk and made the calls, well most of them. There was one he really had no idea what to say to, and it was a talk he thought he should probably have face to face. With that thought he grabbed his keys and walked out, locking the door behind him without looking back. It was time to pay Dean Winchester a home visit.


	31. Chapter 31

**Hello again my sweets. I would like to thank Little Cinch** **for the lovely review.**

 **So here is the next chapter. I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Dean was sitting in his office trying very hard to ignore the slight pounding he had in his head from all the alcohol he had drunk the last evening. He had no idea what had happened with Cas and Gabriel, all he knew was that Cas had walked away from him. And that hurt damn it, it hurt a lot. He really liked the guy. But he couldn't really blame Cas for walking away, if he had been in his position he would have done the same thing. What he and Gabe did was shitty, even if Gabe was the one that instigated it, Dean had gone along with the plans, so he was still to blame. He just wanted a chance to apologise to the guy, he would get down on his hands and knees and beg if that was what was needed for Cas to give his forgiveness.

His issue was he had no way of contacting Castiel. When he had woken this morning and decided he would phone him to say sorry he realised he didn't have the guys number, so he had realised he was going to have to wait until his lesson on Monday. Then he would do anything Cas wanted in apology, audience of Gabriel be damned.

Dean was sitting in his office planning all the ways he would apologise to Cas, hell he would even let the guy take on some fancy loop the loop flying if that was what he wanted, when he heard the roar of an engine coming down the street. Normally only an engine that sounded like it was going to break down caught his attention, but this was sweet sounding, not as sweet as his baby, but still…

Looking up and out of the window he saw a bright yellow Lamborghini pull into his parking lot. With frown he stood to go and greet this customer, though who would bring a car like that to him he was none the wiser. Well that was until he got outside to find Gabriel leaning against the door of it.

"Should have known you'd drive that monstrosity." He said in a not completely friendly tone. Okay he wasn't blaming Gabe, it was his own fault. But the other guy had come up with the freakin' crazy plan in the beginning.

"It's a Lamborghini Dean. You cannot call it a monstrosity." Gabriel replied with a shake of his head at Dean's uncultured attitude.

"I can call it whatever I like. And I was more referring to the colour. Yellow? Really?" Dean asked, cos right now just looking at thing was making his eyes hurt.

"No point having an expensive car and allowing to blend in with the other cars now is there?" Gabriel asked with a sunny smile on his lips making Dean just roll his eyes at the man. He should have known that Gabriel had the poser gene.

"What you doing here Gabe?" He asked with a sigh, turning from the light hearted conversation.

"Cassie came to see me last night." Gabriel said crossing his arms and staring at Dean.

"Yeah?" Dean replied as nonchalantly as he could. When Gabriel just kept staring at him without saying a word Dean found himself breaking. "Sorry, I was drunk and it kinda just slipped out."

"What exactly did you say Dean?" Gabriel asked in an even voice. He wanted to know exactly what had sent Cas on his voyage of discovery.

"That I wasn't in to you, that I had liked him from the beginning and you were as straight as an arrow with a hot girlfriend. Oh and if he wanted answers to google you." Dean replied trying to remember everything he had said in his drunken stupor the night before.

"Thanks for that." Gabriel said sarcasm lacing his tone.

"I'm guessing that bruise on your jaw isn't from walking into a door then." Dean answered with a wince and an apologetic look. He really didn't want to be the cause of Cas and Gabe fighting.

"Not unless my brother fist is actually a door Dean-o, no." Gabriel replied with humour. He didn't blame Dean, hell if anything he needed all the friends he could get right now.

"Sorry. I know I shouldn't have said anything, I made a right pigs-ear of this one didn't I?" Dean responded with a self-deprecating sigh making Gabriel roll his eyes at the man in front of him. Did he take the blame for everything?

"Not your fault Dean-o. Don't blame yourself." He said trying to make Dean feel a little better. Though he kind of doubted that was actually possible. He hadn't found it to be yet.

"Yeah well, I definitely need to share some of the blame. At least I can apologise when I see Cas on Monday." Dean replied with a shrug, though when he looked at Gabriel he saw that the other man was starting to act shifty and look extremely uncomfortable. Which led him to one conclusion. "Are you here to tell me Cas won't give me lessons anymore?" He asked fear in his voice though he tried hard to hide it.

"It's not just you Dean. He quit. Without Cas there's no business. I'll refund your money, no problem." Gabriel replied trying to be as sensitive as he could. He heard the fear in Dean's voice and he couldn't believe how badly this had got screwed up.

"Refund it to Sam, he was the one who paid. Shame though. Cas was actually a really good teacher, when you got beneath the hot, sassy exterior." Dean said putting on his mask of practicality to hide his pain at the idea of never seeing Cas again.

"Is there anything other than that?" Gabriel asked off-handily. He had always thought that that was a perfect description of Castiel.

"Yeah Gabe. There really is. That's just Cas front. A mask, come on we all wear one right?" Dean replied with astonishment. Surely Gabe could see the real man his brother was below the gruff exterior, couldn't he?

"Yeah we do. Look I have to go sort stuff. But I'll keep you up to date and all that." Gabriel said, an idea suddenly coming into his head as he thought of a way to support Castiel without him seeing it as charity. It made sense to Gabriel at least, and he needed to go sort out the plans so he could get it all arranged on Monday morning.

"Wait can I have Cas' number?" Dean asked quickly as Gabriel turned to get back into his car. Of course then Dean cursed his words, could he sound any more pathetic?

"He never gave it to you?" Gabriel asked confused by that. Surely Cassie had given Dean his number, he really liked the guy for god's sake.

"No." Dean responded shaking his head, but Gabriel could see the hope in his eyes that he would.

He thought about it briefly. He could give Dean Castiel's' number and maybe they could sort it out and get together. But then again, maybe it would just make Cassie even more pissed at him for interfering with his life again. No he needed to learn to stay out of Castiel's business.

"Sorry Dean-o. I can't." He finally replied as he evaluated the idea in his head.

"I understand, just if you see him, tell him I said hi?" Dean asked hoping that that would make Cas maybe want to get into contact with him. It was a long shot he knew, but he could hope.

"Not sure he would be too happy with me giving that message right now, but I will." Gabriel replied with a sincere voice. He wished he could do more to help Dean and Cas, that of course gave him another idea, another part of the plan he was going to put into place. But for it to succeed, he would need help.

"Thanks Gabe. Good luck." Dean said with a smile and wave for the guy. He wasn't bad after all, just misguided when it came to Cas.

"You to Dean-o, you to." Gabriel replied and got into his car and reversed out of the parking lot. He had planning and organising to do. He just hoped that it would make things a little better with him and his brother.


	32. Chapter 32

**Hello my angels and demons (no discrimination here). I would like to thank CaptianAckles, Little Cinch and Tie-Dyed Broadway for the wonderful reviews. I would also like to thank all you lovely people who have followed and favoured since my last update.**

 **So here we are the next chapter. This is a short chapter I know, but I felt it was time for a time for a level head. Or maybe not, we'll see. (Evil cackling ensues.)**

 **Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

It was five o'clock Sunday afternoon when Sam finally tracked his brother down to the Roadhouse's bar drinking copious amounts of alcohol. Of course had Dean told him what was going on it would have been the first place he looked, but considering he was under the belief that Dean and Cas had gone on a date (and as Dean hadn't told him otherwise) he had assumed it had gone well. He did not think to look for his brother trying to drown his sorrows.

But now he had found him doing just that. As such the first thing he did was remove him from the bar and drag him back to his place in the hopes that Dean would be able to sober up a bit and explain what in hell had happened now. Cos honestly, Sam was fast coming to the decision that the Novak brothers and Dean were like a bad soap opera.

"What happened Dean?" He asked handing his brother a cup of black coffee, which taking a sip of Dean scrunched his nose at.

"I might have got drunk and told Cas about what Gabe and I were truly up too." Dean responded putting his head in his hands as he realised once again what a major mess he had made, of well, just about everything really.

"Oh crap." Sam replied. There wasn't much else he could say to that really. All he could do was try to help his brother feel better.

"You're telling me. Now I have no way of contacting the guy to apologise cos he's quit the business and everything. It seems I've not just screwed up my life but everyone else's as well. Cheers." Dean said in a self-deprecating tone as he picked up the strong black coffee and raised it in a toast before taking another gulp.

"Dean. Don't be stupid-" Sam started to say, trying to look on the bright side and cheer his brother up.

"What? I'm telling the truth." Dean interrupted. He didn't need his brother trying to put a spin on what he had done.

"No I mean it was Cas' decision to leave the business. Gabriel's decision to lie to his brother. It's not all your fault." Sam explained hoping, though not believing, that it was getting through Dean's head.

"No just that bit that's breaks my heart. Thanks for the pep talk." Dean replied sarcasm heavy on his tongue. He didn't need the perk up 'you never know' talk right now thank you very much. Now was time for wallowing.

"Wait, what? Breaks your heart? Dean? Were you … serious about Cas?" Sam asked incredulous, cos really? He really liked Cas that much? They barely knew each other for god's sake.

"Sammy, if given the chance I'm firmly in the belief I could have loved him as you love Jess." Dean replied with a completely serious tone making Sam's eyes widen. Okay, the situation was completely different to the one he thought he was dealing with. Time to change gears here.

"Wow, okay. That does change things somewhat." He said stunned by his brother's revelation.

"How? Situations still the same, bro. I messed up. I'll deal, just as I always do." Dean responded with a shrug of his shoulders. He didn't see the difference.

"Dean." Sam said in that voice which said talk to me about your feelings, which let's be honest as this was Dean, it really was the last thing he wanted to do, like ever.

"No, I'm fine Sam. just… wallowing. You'd do best to ignore me right now." He said hoping to deflect his brother from the things he may have let slip. Hmm, maybe he should stop drinking, it seemed he told all sorts of things he really wouldn't say when he did.

"Yeah okay, like that's gonna happen." Sam replied with a derisive laugh. Because really? Did Dean really believe he would let go of his brother confessing serious feelings for someone?

"Sam please, just let's talk of something else. How's the wedding planning coming on?" Dean asked trying really hard to change the subject, even though it was no doubt going to fail miserably, just like everything else in his life.

"Its fine and I would prefer to talk about this." Sam answered with a sympathetic expression on his face that just made Dean really want to punch him.

"Well I wouldn't okay? I'm not doing this chick-flick crap. I got myself in this mess. I'm getting what I deserve." Dean replied with venom. It was better that than getting into a punch up when he was drunk. His brother would so kick his ass right now.

"Fine. The wedding…" And with that Sam went on and gave Dean a rundown of all he and Jess had planned since last they discussed it. But at the back of his mind he was trying to think of a way to help his brother get Cas back into his life. The only problem was he could come up with only one solution. And that required him talking to Gabriel. And a junior at a law firm did not get to speak to Gabriel Novak, no matter what the problem. But he would do it, for Dean he **would** find a way.


	33. Chapter 33

**Hello again my darlings. Here have another chapter and everything. It's Monday morning, though not really, cos then I would have to go to work and everything.**

 **Any road, here's it is. Gabriel's plan. Enjoy?**

 **Disclaimer: I don't own Supernatural.**

* * *

Sam was sitting at his desk Monday morning, still trying to work out how to get himself a meeting with Gabriel, when the man in question walked through the door. Sam's jaw dropped. Had thinking about him conjured him up? But before Sam could move and try to intercept the man he was surrounded by the best and brightest at Sam's firm and swept away to the meeting room for coffee and pastries. Sam couldn't even use the excuse of bringing the refreshments into the room, the sectaries always fought over it, saying Gabriel was the only client who ever smiled and said thank you to them. Damn it, just how was he to get to talk to the man?

* * *

Gabriel had been thinking and planning all weekend, and as such he had arrived at his lawyers first thing with the paper work in hand. All he needed them to do was look over it and check its legality and he could get it on its way to the place he really needed it to be. But this wasn't all he had been thinking about this weekend. Yes, what he had a plan that may well fix things between him and Castiel, or at least that was what he hoped, but it would do nothing for Dean and his brother. And he knew that they were perfect together, if only he had left them to it they would be together and happy right now, but what was it people say? Hindsight's a bitch? It was so true in this case. So as he swept into the office he was thinking about how he could fix that as well. And to do that he would need to use his influence.

"Mr Novak, what a surprise, we weren't expecting you. Not that your arrival is an inconvenience I can assure you. We are here for you whenever you need us." The head of the law firm, god knows what his name was, gushed at him making him roll his eyes. Though at least this time that sentence could well be of use.

"Good. I need Sam Winchester. Here. Now." He said in his most arrogant voice so the other man wouldn't even think of questioning him. And it worked, thingy sent his minion to do his bidding in double quick time. Yes there were definitely advantages to having the power he held here.

* * *

Sam was sitting at his desk trying to think of a way to get to see Gabriel when one of his boss's henchman came to his desk.

"Mr Novak is requesting your presence in the conference room." He said before turning and walking back the way he came.

Sam sat there for half a second with his mouth open. Gabriel wanted him? Then he pulled himself together and stood. If Gabriel wanted to see him then that was good. It was time for him to sort out Dean's love life once and for all, no matter what the cost. Thus throwing back his shoulders he marched to the room Gabriel was in and entered, only to find all the top members of the law firm also present.

"Good you're all here. " Gabriel said with a smile when he saw Sam walk through the door. He was sitting in the chair at the head of the conference table where he was swinging backwards and forwards waiting. He wasn't starting this without Sam here.

"So I have drawn up contracts giving Heavenly Wings Flight Training Company to my partner Castiel Novak. He will become the sole owner, and I have also included a generous buy out which will cover the cost for the plane, maintenance and any required repairs, the rental of the airfield for the next six months as well as a generous salary for my brother. I want you to look over it and make sure its water tight. I don't want him to have any way of weaselling out of it, do I make myself clear?" he said in his most commanding tone.

"Yes sir, but well if I might say-" Started thing one, not that Gabriel cared.

"You may not. Leave, read it, rewrite it, I don't care, just get it done. I want to speak to Sam Winchester. Alone." He continued as if the thing hadn't even spoken.

With that everyone but Sam filed out of the room, not before some of them gave the younger man dirty looks, he was going to kill Gabriel for this once everything was sorted out.

* * *

Once they were alone Sam turned to Gabriel with a raised eyebrow.

"Well that's certainly one way of clearing a room." He said dryly, rather amazed that this was the same man he was having a laugh with the other day while Dean had his lesson.

"Yes. One of the benefits of being me. Croissant?" Gabriel asked holding up the plate to the younger man.

Sam just shook his head and sat, waiting for Gabriel to explain why he was here before he argued his case to the man. It was always best to see what the defence had to say before you prosecuted after all.

"So Sam, you heard what I'm doing." Gabriel said getting right to the point. God knows how long his upper hand attitude would keep the wolves at bay.

"Yes." Sam replied. He wanted answers as much as Gabriel wished to give them, he hoped. Because from what he could see Gabriel's plan was crazy, and would not work. But then thinking about it, that seemed to be a running theme involved. How this man had come to be a millionaire was a mystery to Sam that was for sure.

"I want you to deliver the papers." Gabriel stated. He just hoped the younger man would go along with what he said.

"Why?" Sam asked, dashing that hope with one word. Of course he did, he was a frigging Winchester, damn them both.

"Because you can argue Deans case where I can't." Gabriel explained plainly, they did not have time for this.

"What do you mean?" Sam asked confused. If he was delivering papers for Gabriel, how in the hell could he argue Dean's case?

"I mean our brothers are perfect for each other, and I know you know that as well as I do." Gabriel explained as if he was talking to a child. Because come on, wasn't it obvious?

"Then why the games?" Sam challenged him making Gabriel narrow his eyes before he put on his care for nothing persona.

"A miscalculation on my part. But one I'm sure you can fix." He replied with a shrug and a challenge for the younger man.

"I don't know your brother, why would he listen to me?" Sam asked picking at the next point in Gabriel's plan.

"Because you know Dean." Gabriel replied simply. He knew his brother had feelings for the man. If Sam told him how much Dean was suffering (and he knew he was) then surely Cassie would forgive him his part and they would be happy.

"Why don't you just… I don't know… apologise?" Sam asked sarcasm dripping from his lips. He couldn't believe this man, was he really that insane?

"Never say you're sorry. It's a weakness Sam. And one I'm not willing to show." Gabriel response was absolute. Sam knew no matter what he said Gabriel wouldn't hear it. That was just the way he was.

"Even if you lose your brother because of it?" Sam asked. Even if he knew it was pointless, he had to try right? Surely being family meant you made mistakes and then apologised for them. At least that was what dean always taught him.

"We're not there yet, and we're not going to be. Deliver the papers Sam. go sort them out and get them together. I failed, maybe you can succeed." Before Sam could open his mouth to respond to that the door opened to reveal thing one once more who wanted to check a few facts with Gabriel before he had the contract sent to print. Sam became nothing more than a wall hanging during that conversation. By the end of it it seemed that Sam's status as delivery boy was confirmed with not just Gabriel but the firm. He didn't really have a choice but to deliver the papers now, but he really did think that Gabriel was going about this the wrong way. Completely the wrong way.


	34. Chapter 34

**Hello my bunnies. I would like to thank** **Tie-Dyed Broadway** **and Little Cinch** **for the lovely review. I would also like to thank those of you who have followed and favoured since my last update.**

 **So my 'plan' says I have about 5 chapters left, after this one. (Though those who know my 'plans' know that can be a fluid assessment on occasion.) So just giving you warning, we are approaching the end. Though we have some way to get there. A lot can happen in five chapters, believe you me.**

 **Anyway enough about the future. Here's the present. Enjoy the new chapter.**

 **Disclaimer: I don't own Supernatural.**

* * *

It was Monday afternoon and Castiel had spent the day doing absolutely nothing. In fact he revelled in it. Nothing was his bread and butter right then. Of course he had got bored after an hour of it. But still, he would not cave. He would not call his brother, and he would not call Dean. But god damn he was bored as frigging hell.

Just then his phone alerted him to an email, but before he could open it to read there was a knock at his door. What was this, not one try's to contact him all freaking day then two at once? It was like bloody buses. With a frown he felt he should probably answer the door first, though when he opened it and saw who was on the other side he wasn't sure he had made the right decision. Turning from the door leaving it open without a word he made his way back to his living room. He didn't need this shit. Whatever this shit was, he was sure he really didn't need it.

* * *

Sam had been shaking his head in disbelief as he made his way up to Castiel's apartment, there was no way this was going to work. As such he was pleasantly surprised when the other man didn't slam the door in his face. Though he was rather disconcerted by the fact that Castiel just walked away from him without a word. Entering the apartment and making his way to the living room he found Castiel slouched on the couch with his phone in hand.

"What do you want?" Castiel asked without any sort of greeting. He really couldn't care less about being polite to this douchebag. He was Dean's brother. Hell he had probably been in on the whole thing. That was probably what he and Gabriel had been laughing about when he had taken Dean for his lesson.

"Um, hi, Castiel. Your brother asked I give you these." Sam said unsure as he held out the brown envelope that contained the contracts for the Heavenly Wings Flight Training Company.

"What are they? Family divorce papers? Cos if so I've already disowned him." Castiel replied with a sneer not looking up from his phone. He was busy reading the email that had just come through. The email that could get him out of this shit whole and this whole business.

"No, there the deeds for the company. Gabriel has made every over to you so you are the sole owner. He's also put up the capital so you can get yourself back on your feet." Sam replied, though he cringed at the words. He dreaded what Castiel's response to that sentence would be.

"Well tell him thanks, but no thanks. I have another job. Just got back the offer, I start in two weeks. So I'll be out of his and Dean's hair then." Castiel answered finally putting down his phone and giving a Sam a look that said 'I don't give a flying monkey' about what my brother or yours is doing. I can make it alone, see.

"Dean doesn't want you out of his hair." Sam answered, screw Gabriel he was here for his brother. Not his career.

"Right, he just lied to me because he thought it was the best way to get me? Please, I'm not stupid Sam. your brother doesn't like me. He likes games, and I am refusing to freaking well play." Castiel replied sarcasm dipping from his lips as he formed them into a sneer which Sam really didn't like to see.

"No you're wrong, he does like you Cas. More than even I knew." Sam defended passionately. He needed to get through to this man, make him see what Dean truly felt for him.

"I don't care." Castiel dismissed Sam's passionate plea with the wave of a hand.

Sam was about to explode at the man for being so careless with his brothers emotions when he noticed something. Castiel had not looked him in the eye when he had said that sentence. As such he took a punt on his hunch.

"Yes you do. You are a terrible liar." He said with a confidence he didn't truly feel.

"Unlike your brother?" Castiel asked with bravo. But Sam could see he that he had him caught. Time to reel.

"He messed up, okay. He accepts that. But he really does like you Castiel. More than I have ever seen him like someone before." He said with complete sincerity in his voice, hoping that the other man would believe him.

"How can I believe a word of what you say Sam? Tell me, cos I'm not buy what you're selling here." Castiel replied with a sigh. God he wished it was true. He had actually liked Dean, more than he had ever liked anyone in his life. Hell he had been willing to give him to Gabriel for Christ sake. He wasn't going to do that with someone he didn't think was worthy. And he really had thought Dean was worthy. In the days since he had heard the truth he had admitted to himself that the guy in the bar, Crowley, was right. He had been jealous, he had wanted Dean for his own. And look where that had got him, the freaking dung heap, that's where.

"I don't know. All I know is what Dean told me." Sam replied trying his hardest to get Castiel to see the truth of Dean. Not what he had seen.

"Oh yeah? And what's that?" Castiel asked in disbelief. Did this guy really think that would work?

"That he could, given the chance, feel for you as I do about my future wife." Sam said, repeating Dean word for word while apologising silently in his mind to his brother. Though if this worked then Dean would so owe him one.

"I think it's time you left." Castiel stated. He didn't want to hear this shit. He didn't want to hear Sam sprout on about how Dean had feelings for him. The man did not give a flying… pig for him. So his brother could stop, right now. Whatever game he was playing, and considering he came baring Gabriel's papers it was no doubt one of his brothers, he did not care. He was gone, out of here, in two freaking weeks and he couldn't wait.

"Fine. But here's the papers. Think about it. Don't throw away what could be just because you're pissed." With that Sam placed the envelope on the coffee table and left. He had done what he could. It was up to Castiel now, he just hoped the man didn't act in a 'cut of your nose to spite your face' way. He had nothing else, no more cards to play. He had played Gabriel's hand as well as his own. He just hoped that the Novak brothers got their heads out of there asses before it was too late and hurt his brother irrevocably.


	35. Chapter 35

**Hello again. I just couldn't stay away, or go to bed, whichever you prefer. I would like to thank** **Tie-Dyed Broadway, rainystv** **and Little Cinch for the lovely reviews. I would also like to thank those of you who have favoured and followed this story this my last update. I love you all.**

 **So next chapter I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel sat there for two hours, staring at that god damn brown envelope without opening it. When he realised what he was doing he decided it was time to leave. He was not going to look at what his brother had oh-so-generously given him. With that he grabbed his jacket and left his apartment. Walking aimlessly down the sidewalk. Or many be not so aimlessly, he thought as he found himself once again outside that British bar, with the man who kept giving him advice. He still wasn't sure if he should class the guy as wise or freaking delusional and crazy. But either way, a good glass whiskey, or ten, wouldn't go amiss right now. With that Castiel pushed open the door to find as he cased the room that yes, Crowley was sitting in his usual stool at the bar. Whiskey glass in front of him. Making his way to the bar Castiel pulled himself up to a stool next to the dapper British man. Signalling the barman he ordered a bottle of whiskey and turned to Crowley to find the other man looking at him with raised eyebrows.

"This could take some time." He growled at him making Crowley smile.

"As you wish kitten. But I'll pay." Crowley replied placing the money down for the barman before he turned back to Castiel.

"So, tell me your secrets, your wishes and your dreams. Talking costs nothing after all."

And Castiel, who was so desperate to talk to someone he didn't even see the slight predatory look in the other man's eyes as he filled up both there glasses, did just that. Telling Crowley everything he had discovered and everything that had happened because of it.

At the end of his tale, both he and Crowley took a long drink of the whiskey in there glass. The whiskey in the bottle had depleted rather rapidly during the explanation, and Crowley had seemed to drink most of it. Listening did that.

"Well Gabriel Novak-" Crowley started to say but Castiel interrupted him. He wasn't that drunk that he didn't know what he had said. After discovering what a public figure his brother was he knew that he would never give his brother's name in relation to this tale.

"I never told you my last name." he growled at the man next to him narrowing his eyes. Just who was this Crowley?

"Oops." Crowley replied with a casual shrug, taking a drink of whiskey so he could think over what to say next.

"Who are you and how do you know my brother?" Castiel asked even more suspicious now. He knew that rich people attracted attention. Was this guy some sort of reporter who would publish all he had said?

"You know who I am kitten. And as for your brother? Let's just say we're… acquaintances. In our world friend are few and far between after all." Crowley responded and then just looked at Castiel waited for his judgement.

Castiel looked at the man and analysed his words. He remembered how the man had reminded him of his brother. So yes he could easily put this man in the same category as Gabriel, a business man. Not that excused what he had done at all.

"You used me. To get recon on Gabriel." he growled at his drinking partner pulling the bottle towards him though he knew it was far too late. He had told this man much more that Gabriel's competitor should ever know. He had given him the ammunition to annihilate his brother, and he suddenly realised that while theoretically that may have been what he wanted a few hours ago, he didn't want that now.

"While yes, that may well have been my purpose at the start. Now I'm not so sure." Crowley replied with a frown. He didn't even understand his own mind sometimes.

"What do you mean?" Castiel cautiously. He did not trust this man anymore.

"I may not be your brother's best friend but I will say this for the man. He always fights an honest battle. And he always does what he believes is right. Whether anyone else agrees with him, is a question up for debate." Crowley said in lieu of answer as he took another sip of the whiskey in his glass.

"Are you saying I should give him another chance?" Castiel asked his mind going crazy trying to work out this guy's angle, while having drank far too much.

"I'm saying that I like an even playing field. At present your brother is playing handicapped." Crowley replied with a frown. He couldn't believe he was even thinking what he was saying, let alone actually saying it.

"I don't understand." Castiel replied even more confused.

"Oh come on kitten. You and I know that this isn't all about your brother and Dean right?" Crowley answered. It was obvious to him. Surely at least one of those involved saw the truth, right?

"It's not?" Castiel asked, still extremely confused, but hoping that if he discovered Crowley's angle he would be able to save his brother.

"No Castiel, it's not. You have spent the last 15 years living under the rule of don't ask, don't tell. Yes I know exactly who you are and what you have done. Tell me, have you ever actually had a relationships before?" at that Castiel just glared at the man, how dare he question him about that.

"I thought not. If this was just about the lying then yes you would be pissed, but you wouldn't be running. That is the sign of someone afraid of commitment." Crowley finished with a gusto as he downed the whiskey in his glass.

"You have no idea what you're talking about." Castiel growled standing ready to walk out on this idiotic man.

"Don't I? Are you sure of that Castiel Novak? I was right about family. They really are the most important thing. But it doesn't matter what I say does it. What matters is what is in your heart. Do you really want to see Dean go off with someone else? Because he is a man ripe for the picking from what you have told me." Crowley replied with a smirk on his face making Castiel move closer so he was in the other man's personal space. Not that that seemed to effect either of them.

"You stay away from him." He said in the low voice he had picked up from his brother. But it seemed it had as little effect on this man as it would have had on Gabriel himself.

"Make me kitten. Make me." Crowley answer with a laugh causing Castiel to turn and storm out of the bar leaving Crowley with the rest of the bottle of whiskey. **Castiel did not need this shit right now.**


	36. Chapter 36

**Hello my lovelies. I would like to thank Tie-Dyed Broadway, Little Cinch and rainystv for the lovely reviews. I would also like to thank those of you who have followed and favoured since my last update.**

 **To answer a question the name of this story didn't technically come from the song by Frank Sinatra, but it kinda did. It was what came to my mind when I came up with the plot idea and sort of stuck, I couldn't think of anything else more appropriate (Just like my latest story Take a Chance on Me I kinda stole from Abba). Though I should say I don't seem to be able to read the title without sining it, even if it's the only line of the song I know.**

 **Anyway here's the next chapter, I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Gabriel was sitting in his office looking out over the view he had of the town. Though he didn't see it. He was trying to think of what he could do to keep Castiel here. Sam had relaid what his brother had told him about having another job and leaving to two weeks and Gabriel's first response was to find out who had hired Castiel and get them to change their mind. But he didn't do it. He was learning, slowly but still learning, that he really shouldn't meddle in his brothers life. He just wished he could do something to make it all better again. Make it how it was before it had all blown up in all their faces.

Just then there was a knock on his door which confused him. Everyone else had long gone home. Looking up he found the last person in the world he wanted to see standing in his doorway.

"What the hell are you doing here?" He growled in exasperation at his visitor, who took that as an invitation to come in and sit down, placing a half finished bottle of whiskey on Gabriel's desk and looking at him expectantly. Gabriel sat there and stared back before rolling his eyes and going to get two glasses and slamming them down by the bottle without another word.

"How welcoming. While it may be true we're not exactly friends, I have recently become your brothers confidant." Crowley replied dryly pouring them both a glass and offering one to Gabriel who was looking at him in shock.

"What?" Gabriel asked automatically taking the glass from the other man.

"I know, I'm as surprised as you, believe me." Crowley answered sitting back and taking a sip of his whiskey.

"What do you want?" Gabriel asked with a sigh. No doubt Crowley had an angle here. He always did, Gabriel should know, he'd known the guy for years after all.

"Surprisingly to help you." Crowley replied with a look of disbelief at his own words on his face.

"Why?" Gabriel asked his eyebrows raising in shock. That was not a sentence he ever expected the other man to utter.

"I like to play it clean Gabriel. you of all people know that." Crowley answered straight. To was the truth, though why he felt the need to get involved in this he still hadn't figured out.

"So?" Gabriel asked cautiously, what was Crowley getting at here?

"So, apologise to your brother. It is the only way you will make it up to him." Crowley replied with a roll of his eyes. Was he the only one who could see that?

"And Dean?" Gabriel asked leaning back and enjoying his whiskey and this strange circumstance of Crowley giving him advice. Whether he took it or not was a different matter. He did not apologise after all.

"That is a problem you can't resolve. Castiel is scared of commitment, but you knew that already. Hence the subterfuge." Crowley answered, telling Gabriel what he really already knew. There was nothing he could do to fix Castiel and Dean, he just wished there was.

"True." He finally replied with a sigh his eyes returning to the view.

"Well I've said my piece, as of tomorrow, its back to business as usual." Crowley said standing placing his glass on the desk.

"Agreed." Gabriel nodded at the other man and watched him walk out of his office. Looking at his desk he noticed that Crowley had left him the whiskey, how thoughtful. He had a lot to think about it seemed.

* * *

Castiel returned to his apartment. He couldn't believe how stupid he was to have told a complete stranger his family business. God knows what Crowley would do with it, even if he said he would do nothing Castiel did not trust him. And then there was his very thinly veiled threat that he would go after Dean. Castiel wouldn't let him anywhere near his man. But what could he do about it really? He was leaving in two weeks to go and fly pretentious pricks, just like Crowley, round the frigging country. Oh god, what was he doing?

It was at that point he reached his couch and fell onto it. In the process of doing so his eyes caught sight of the brown envelope still on his coffee table where Sam had left it. He contemplated it for a few minutes before, with a heavy sigh, he gave in and picked it up. Opening it he read through all his brother had given him. It was there for the taking, the question was, could he do it? Because taking this would not just be him taking the business, but it would be him showing Gabriel he had forgiven him, and Castiel was definitely not there yet. He wasn't sure if he would ever be there.

Running his fingers over the papers he let his mind turn back to the thing that filled his thoughts it seemed. Dean. Was he really running away because he was scared of commitment? He really did like the guy, and if Sam was correct, Dean really liked him too. So what was the problem other than Castiel couldn't trust him? Was there one? A relationship needed trust in his mind. Without concious thought all the words told to him by Dean, Gabriel, Sam and Crowley about him and Dean rose in his mind. It seemed his brother had thought as Crowley did, that he would run from anything serious. Where they right?

And well, as for Dean, he knew his brother had the ability to get anyone to do anything if he put his mind to it. He remembered when Gabriel had asked Dean out for there second date and Dean had looked very much like he didn't want to go. Gabriel really had been the driving force, but still... Dean went along with it. Oh god, there was too much stuff going through his mind. He just wanted it to stop. With that he got up, leaving the papers on the table and decided to go to bed. Maybe a nights sleep would help him figure some of this craziness out.


	37. Chapter 37

**Hello again my dears. Have another chapter, I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel woke the next morning just as confused as he had been before he had gone to sleep, and he knew of only one solution to when he felt this way. He needed to fly. With that thought he grabbed his keys and left his apartment, not once looking at the papers on his coffee table.

He arrived at the airfield and went straight to the hanger, he needed to be in the air like, yesterday.

* * *

Gabriel was sitting at his breakfast table reading through some work when his phone went alerting him to a text message. See being the man he was he had spies everywhere, and it was one of them, texting to inform him that his brother had just arrived at the airfield. Jumping up he grabbed the keys to his Lamborghini and was out the door. He didn't know what he was going to do or say, all he knew was he needed to see his brother.

* * *

Castiel was busy doing the preflight check, however much he wanted to be up in the air he couldn't cut that down, when he heard the door to the office go. He ignored it, along with the voice calling his name.

* * *

Gabriel entered the office to find it empty, but that didn't really surprise him, if his brother was still here he would be with his angel. Making his way to the hanger he saw his brother walking around the plane doing god only knows what.

"Castiel." He called as he entered, hoping for something, even if it was just his brother telling him to get lost. But all he got was silence. Castiel didn't even turn round. Running his hand through his hair in frustration Gabriel had no idea what to do or say to get his brother acknowledge him but he knew he had to try something, as such he opened his mouth without thinking about what was going to come out of it.

"I'm sorry Cassie."

At those words Castiel stopped what he was doing in surprise. Had his brother really just said the S word? Turning he looked at Gabriel to see the same look of shock on his face as Castiel felt on his own. Seemed his brother hadn't planed to say it then. For some reason that made Castiel feel even better about the words. It wasn't one of Gabriel's ploys to get him to do what he wanted. Tilting his head he stood there staring at his brother thinking.

Gabriel just stared back. He refused to take it back or back down. Yes he may never apologise, but now he had he wasn't going to expand on it, or grovel. Hell no. Gabriel Novak did not grovel to anyone.

With a nod Castiel turned back to his angel before he spoke.

"Want to come for a flight?" He asked in an offhand manor but Gabriel knew it was his attempt at an olive branch and he was not about to throw that away.

"Sure." He replied letting out the breath he hadn't known he had been holding before making his way round to the passenger side of the plane and getting in.

They didn't speak again until they were up in the air.

* * *

"What are you sorry for?" Castiel asked once he had got the plane at a good cruising altitude.

"Everything. The lying, the plots, all of it." Gabriel answered, that wasn't grovelling, it was explaining.

"Including Dean?" Castiel pressed, his hands tightening on the stick. If he didn't like his brothers answers, then his brother would not enjoy this flight so much. Or though, maybe he wouldn't anyway.

"Definitely including Dean. I just got carried away at the idea that you and he were perfect for each other," at that Castiel turned to Gabriel with a glare and sharply moved the plane causing Gabriel's arms to automatically grab at the side of the plane. "But I'll keep my nose out of your business from now on." Gabriel rushed to continue. Maybe having this conversation in the air with a pissed off expert pilot wasn't the best idea he had ever had.

"Good." Castiel nodded. Suddenly he pulled back on the stick making the plane go straight up into the air and over in a perfect loop the loop. Of course, he had given his passenger no warning that it was coming.

"What the hell Cassie?" Gabriel screeched at him making Castiel smile in a predatory way. His brother was in his domain now.

"Sorry, did I forget to mention I'm practising my aeronautical manoeuvres today?" He asked Gabriel innocently before turning the plane so it was plunging towards the ground.

"Son of a bitch, you just want to make me puke my guts up." Gabriel growled as Castiel leveled off with a manic grin.

"If you are sick in angel, Gabriel, you are cleaning her up." Castiel replied cheerfully. Oh yes this was definitely fun.

"I'm sure I can find someone to pay to do it." Gabriel muttered causing Castiel to sharply turn so they were horizontal with the earth. "Will you stop that." he demanded. Gabriel really wasn't sure how much of this he could take, damn his little freaking brother.

"No." Castiel replied simply before turning once more.

"I hate you Cassie." Gabriel uttered through gritted teeth. He was going to have to keep his mouth closed if his brother continued.

"You know what they say Gabriel." Castiel replied causally pulling the plane up for another loop the loop. "Revenge is oh so sweet."

Gabriel had no response to that. Not just because yes okay Castiel might just have a point with that one, but mainly he was worried that if he opened his mouth he really would puke. Instead he sat there with his eyes closed tight holding onto the sides of the plane for dear life hoping his brother felt he had punished him enough as soon as possible. He just really wanted to get back onto solid ground.

And when they did get back down Gabriel actually got down on his hands and knees and kissed the floor, making Castiel laugh loudly, seemed he had found Gabriel's weakness now. And it was something he was definitely going to remember for the next time his brother pissed him off.


	38. Chapter 38

**Hello my dears. I would like to thank Little Cinch and rainystv for the lovely reviews. I would also like to thank those of you who have followed and favoured since my last update.**

 **So here's the next chapter I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Half an hour after returning from his fun and wonderful trip into the sky with his brother, and Gabriel was sitting behind what used to be his desk drinking a cup of coffee and finally feeling like he was going to be okay, and that his stomach had finally decided which way was up and it was stick with it. Which was a good thing considering it was at that exact time that Castiel walked into the office from the hanger having put his angel back to sleep.

"Cassie, can we talk?" He asked in what he hoped was a gentle voice, he still wasn't one hundred percent sure that his brother had forgiven him for what he did.

"Yes, since we were children." Castiel replied dryly raising his eyebrow at his brother. Since when did Gabriel make that sentence a question? Was he still feeling guilty? Well good. Serves him right. Not that Castiel held a grudge at all.

"Castiel." Gabriel said with exasperation colouring his tone. How Cassie could be so flippant after that flight he had no freaking idea, and in truth really didn't want to know.

"What about?" Castiel responded with a sigh flopping himself down in the chair opposite Gabriel's with his arms crossed. He hated talking, and in truth he still wasn't sure about everything. Some things have become clearer, but others were still as murky as they were before he went up in angel.

"The business." Gabriel replied. He needed to know what was going on with it, and now that Castiel seemed to be talking to him, it was probably a good place to start. Though when all Castiel did was stare at him he wasn't so sure he was right on that.

"Have you signed the papers?" He asked hoping to get an idea of where they were.

"No." Castiel said cynically and with no emotion.

"Are you going to?" Gabriel asked hoping that after their talk Cassie would say yes.

"I don't know." Castiel replied honestly, it was one of the things he was still trying to work out. He had decided that he would like to stay here, doing what he had been doing a lot more than flying pretentious idiots around, but he really didn't want to have to be any more polite to people than he was, and if he owned this place he was going to have to do all the nasty paperwork and everything. And well, let's be honest, all Castiel truly wanted to do was fly.

"I don't want you to leave Cassie. You're my brother, I kinda like having you around." Gabriel said in a gentle voice, hoping to persuade Castiel to take the company rather than the other job. But he wasn't going to say any more, he knew if he pressed his brother he would do the opposite to what he wanted just to piss him off. It was Castiel's way.

And so the two Novak brothers sat there just staring at each other, and staring, and a bit more staring, until Castiel rolled his eyes and spoke.

"Fine, I'll stay, but only if you keep the company." He said with a put upon tone to his voice as if he was giving his brother a great concession.

"Excuse me?" Gabriel asked his eyes going wide. He really didn't think his brother would want him anywhere near this place and yet, he wanted them back to working together?

"I can't run this place Gabriel. I fly. That's what I do. It's all I want to do. The rest of the admin stuff I am **really** not interested in." Castiel responded with feeling. He just wanted to fly his angel and to hell with the rest in all honesty.

"Okay fine. Then I best get to calling our clients and informing them we're back in business." Gabriel said with a chuckle at his brother's heartfelt declaration that he would not be doing anything in the office. Oh well, at least now Gabriel could call up some of his rich friends and get them flying with Cassie without his brother questioning it. He would get this company up and running with major profits in no time. It was what he did after all.

"Good." Castiel replied standing deciding that this conversation was over and making his way into the hanger, if he was coming back he would need to make sure he had everything he needed to teach flying once again. But before he could take two steps Gabriel spoke once more making him stop dead where he was.

"And Dean? Should I call him?" Gabriel asked as casually as he could, but he saw the tensing of his brother's shoulders at the name and he just crossed his fingers and hoped that Castiel would give Dean another chance, just as he was giving him one. What he had done was worse after all.

Castiel on the other hand was thinking. Dean was the murkiest subject in his mind right now, and He had no idea what as going on between them, he didn't even know if he wanted something to be going on, but he did know he needed to sort this out. He couldn't go on with all the questions and feelings going round in his head. He needed clear cut straight forwards answers, and the only way to get them was talk to the guy. So taking a deep breath he turned to his brother and spoke.

"I'll call him." He said turning round to Gabriel with a fire in his eyes making Gabriel supress the smirk that wanted to emerge onto his face.

"Okay. Here's his number." Gabriel replied with a raised eyebrow instead and then watched his brother walk away to the hanger. Oh my god how much did he want to be in on that conversation? To be a fly on the wall and overhear the lot. He was sure it was going to be explosive.

* * *

Castiel nodded as Gabriel handed the number and he looked down at the piece of paper in his hand. He then as if in a daze made his way to the hanger, he needed privacy to work out what he was going to say and then make the call. It was time to work out just what he and Dean meant to each other.


	39. Chapter 39

**Hello my angels. I would like to thank Tie-Dyed Broadway, Little Cinch, rainystv and CaptianAckles for the lovely reviews. I would also like to thank all you lovely people who have followed and favoured since my last update.**

 **So this is the penultimate chapter, then the epilogue. So I hope you like it.**

 **Disclaimer: I don't own Supernatural.**

* * *

Dean was sitting behind his desk in his office staring despondently at the wall thinking of the one thing that seemed to take up all his mind theses days. Cas. he was the first thing Dean thought of when he woke up and last thing he thought about when he slept. See Sam had also told him that Castiel was planning on leaving town to go to another job, and Dean knew that meant it was over between them before it had truly even begun. He had royally screwed up the best thing that could have ever happened to him by being a complete and utter idiot. There was nothing he could do to change it. There were no second chances in this one. And there was no one to blame but himself.

He was pulled from his depressing thoughts by his phone ringing, he was tempted to ignore it, and if the caller ID had said someone he knew, Sam for instance, he would have done. But the number wasn't one he recognized and as such he knew it could be work related. So forcing all thoughts of Castiel from his mind he answered the phone.

"Hello, Dean Winchester speaking." He said in an as professional tone as he could manage when all he really wanted to do was go and drown his sorrows.

"Hello Dean." Came the deep gravely voice down the line that he had never expected to hear again. He almost dropped the phone in surprise.

"Cas." He breathed down the line, as if he spoke it too loudly the man on the other end would disappear.

"Yes. Are you still interested in learning to fly?" Castiel asked briskly. Making Dean's heart sink. This wasn't about them, this was about Dean and his bloody fear. He wished he had never even mentioned his fear to his brother, then none of this would have ever happened. Though he knew at the back of his mind that no matter how painful, he couldn't really wish he had never met Cas.

"Yes." He finally replied hiding the hurt as best he could.

"Then come to the hanger tomorrow morning at 10 am." Castiel responded in his no nonsense tone.

"Okay I'll-" Dean started to reply but the line had gone dead. Castiel had hung up. And Dean well he just turned the phone to him and looked at it. Had that really just happened? Was he really seeing Cas tomorrow morning? Because he knew, even if this was only for a lesson, it was also the only chance he was going to get to try to get the other man to give him a second chance. And that was all he had wanted after all. So he was going to have to plan what he was going to say, and screw the consequences, if all Cas did was laugh at him and tell him that he felt nothing then so be it. At least then Dean would know and would be able to let the dreams go. Or at least he hoped he could.

* * *

Castiel nodded at his phone as he hung up. He had realised while staring at the number Gabriel had given him, that him and Dean really needed to have the conversation about them face to face. As such he had arranged one. But for now it was time to make sure he had all he needed for Dean's lesson tomorrow, for even if nothing happened between him and other man or they decided that they didn't want each other he still had to get the guy over his fear of flying so he could attend his brothers wedding. With that in mind he went back to the office to inform Gabriel that from 10 onwards tomorrow he would be busy without mentioning why, and then left to go and purchase the one thing he thought might just help Dean Winchester, he hoped it would at any rate.

* * *

Dean had woken the following morning with equal parts excitement and dread in his stomach, but he forced himself to relax. He could do this. He had decided it would be best to take the day off of work and as such had got one of his mechanics to cover, that way if things went well with Cas maybe they could spend some time together, of course it also meant if they went badly he could go drown his misery without any worry about anything else. He dressed with care, choosing his best shirt and jeans, hoping that if he looked good then Cas might listen to what he had to say. Taking a deep breath he looked at himself in the mirror once more to check everything was good and then grabbed his leather jacket and car keys and made his way out of the door. Time to go and face the music.

* * *

Dean walked into the office unsure of what to expect. And he certainly got a surprise. For there in his usual seat was Gabriel. The Novak's must have made up then, well that was a good sign for Dean. If Cas could forgive his brother surely he could forgive him as well? Of course different rules applied to family, Dean knew that better than most.

"Hey Dean-o. Well I must say, this certainly explains things." Gabriel said looking up when the door opened to see Dean Winchester standing on the threshold. The sight made a genuine smile appear on his face.

"It does?" Dean asked confused by that sentence, what was Gabriel talking about?

"Yep. He's in the hanger." Gabriel replied refusing to be drawn. He had made the decision to stay out of Cassie's business and he was sticking to it. No matter how hard he was finding it. He wanted to tell Dean that Castiel had cleared his day for him, that his brother was wearing his nicest, smartest clothes for him. But he didn't, Dean was just going to have to work that out for himself. Gabriel was _not_ getting involved. Not again.

At that sentence from Gabriel Dean nodded and taking a deep breath and throwing his shoulders back he made his way to the door, his hand briefly resting on the door handle as he got into his mind all he wanted to say. Once he had it sorted he took another deep breath for courage and pulled the door open and walked through.


	40. Chapter 40

**Hello my sweetlings. So here it is the last chapter excluding the epilogue. I would just like to take this time to thank all you wonderful people who have taken the time to review this story. You are all awesome and motivate me to write more, challenge me to think of the next step on my story's journey, and for that I am forever grateful.**

 **I would also like to thank those of you who have followed and favoured this story, it feels amazing when I get those notification emails, to know that people are enjoying my writing, so thank you all very much.**

 **Anyway enough from me. Time to see what happens between Dean and Castiel this time. Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

Castiel was working in the cockpit when he heard the door to the hanger open. Looking up, he saw Dean's silhouette before the man entered and looked round the hanger. Castiel didn't say a word. He just took in vision that this man presented. He truly was the most beautiful man Castiel had ever seen. And he could be his, if he wanted him.

"Cas?" Dean called out into what seemed to be an empty hanger, was this some kind of joke?

"Hello Dean." Came a voice from the area of the plane, which thinking about Dean guessed he shouldn't have been surprised about. Then he watched the man who had filled his every waking (and sleeping) thoughts for a while now. He watched as Cas climbed out of the cockpit and wiped his hands on a rag. He watched how his shirt tightened as he moved his arms, and how his jeans hugged his lower body, and all of Dean's carefully planed out words deserted him as his mouth went dry. But he knew he had to speak, he had to convince Castiel to give him his second chance.

"I'm sorry Cas. I mean it. For everything. I know I shouldn't have gone along with Gabriel's plan. I should have been straight with you. But I couldn't. I mean look at you. You're amazing, you're sexy and funny and clever, and why would a guy like that be interested in me? So truthfully I thought I had no change, and Gabriel well he's really good at getting people to go along with him. I didn't really think. I know that none of that's an excuse, I'm not trying to use it as one. I just... I need you to understand. I am so, so sorry." Dean rushed to say. At the end of his verbal diarrhoea he was out of breath and just staring at the man who had come to mean so much to him in such a short amount of time.

"Well that was unexpected." Castiel replied raising his eyebrow at Dean. He certainly hadn't expected Dean to be so upfront with all that, he had thought he would have to take Dean in the air to get anything from him, seemed he was wrong. Maybe Sam was right and Dean really did like him. The question was how much did Castiel like Dean back? And was he willing to give a relationship with the guy a go?

"Was it?" Dean asked confused as to why Cas wasn't expecting that. Surely he had expected an apology right?

"Yes." Castiel replied with a smile at Dean's confusion. He really was like no other man that Castiel had ever known. He liked that, it was refreshing.

"Was it also unwelcome?" Dean asked nervously. He really hoped not. Seeing Cas again just made him realise how much he really liked the guy.

"That I don't know. But how about after your lesson we go for a coffee and talk about it more?" Castiel suggested in an offhand manor, even if he had taken a deep breath before he spoke. This was him taking a chance on something, he just hoped he was doing the right thing.

"Coffee?" Dean asked his eyebrows raising, did that mean what he thought it meant? I mean was that like coffee, or was it _coffee_?

"Yes Dean. You know that caffeinated substance that people drink?" Castiel replied sarcastically with a smirk for the other man.

"Like as in a date, coffee?" Dean asked after taking a deep breath. Well you know, if you don't ask you don't get and all that.

At that Castiel tilted his head and looked at the hope in Deans eyes. Until this moment he hadn't known the answer to that question, but now he did. Because he had just realised there was something he really wanted to do right now. So with a smile he walked closer to Dean before he replied.

"Yes, Dean. As in a date." With that he took one more step and put his hands either side of Dean's face and pulled him down so that he could place his lips on top of the other man's. It had a surprising effect, as soon as there lips touched in that kiss Dean seemed to melt against him, wrapping his arms around Castiel.

* * *

As soon as Cas' lips met his Dean knew that he was home. He was happy, he could take on the world as long as he had this man at his side. As such he wrapped his arms around him, not wanting to let go, ever.

And Castiel, well, he moulded Dean's body to his and deepened the kiss. It was like nothing he had experienced before, and he had kissed quite a few men in his time, but this, this was different. This was warm and inviting, and had no agenda attached. This kiss was purely for the pleasure of feeling Dean against him. And he realised that that was exactly where he wanted him to be for the rest of his life. Yes, this was what he wanted, he wasn't going to run from this any more. He couldn't even if he wanted to. He had a feeling that his life was fast becoming to depend on the man in his arms.

Castiel finally pulled away and rested his forehead against Dean's, taking note of the slight flush on the other man's cheeks and the massive smile on his lips.

"You have a lesson Dean. Stop distracting me and get into the plane." he murmured, not that he moved away from the other man.

"I much prefer the distraction to flying." Dean responded cheekily making Castiel chuckle and pull away from him and turn and walk towards the pilots side of his angel.

"You know Dean, play your cards right and I might just end up agreeing with you. Now get you cute ass into my angel." He answered over his shoulder with a saucy wink for his man.

"Yes sir." Dean replied still smiling as he bounded towards the plane and climbed in without thought. If Cas was getting into the plane then Dean was going to follow him. Whether he survived his fear or not was another matter. But he would have Cas at his side, he could do this with him there.

* * *

They took off and Dean tried to keep his breathing as even as possible by looking only at his pilot.

"You know, staring at me like that is a distraction Dean." Castiel said once they were in the air and without turning to the man next to him.

"I thought you were the best. Surely you can mange to fly with a bit of distraction." Dean replied leaning back a smile still on his lips as he stared at Cas.

"Hmm, next time we're driving I'll try it on you. Hit that red button." Castiel responded pointing the red button situation between the two of them.

"Why?" Dean asked, he was pretty sure that hitting red buttons in planes when in the air was never a good idea.

"Hit it and you'll find out." Castiel responded with a smirk. He wasn't going to tell Dean his plan for helping Dean overcome his fear. Or at least a solution that was different to staring at him at any rate. Not that he minded Dean staring at him, except it gave him all sorts of ideas that he really couldn't act on while piloting a plane. He wasn't _that_ good.

And so Dean hit the button. He trusted Cas, and if he told him to do it, he would. suddenly the cockpit of the plane was filled with the sound of the song Danger Zone.

"Really? Top Gun much?" Dean chuckled happily, he could cope with flying if he had his angel and his music.

"Want me to do some moves from the movie?" Castiel asked innocently gripping the stick as if to bank to the left.

"Hell no." Dean squeaked. Okay so he had accepted normal flying, but that shit was never happening while he was in the plane thank you very much.

With that they both slipped into silence, a smile on their lips, as the music filled the plane, switching from that one song to Metallica which Dean started humming along to. And Castiel looking over at him smiled even more. It seemed his plan of giving Dean music to take his mind of his fear was working, though if asked Dean would claim it was more to do with his pilot kissing him before they got into the plane that had relaxed him so much.


	41. Epilogue

**Hello my darlings for the last time.**

 **So here we are, the epilogue. The end of the story. Again thank you to all of you who have supported this tale. I hope you like my ending.**

 **Enjoy.**

 **Disclaimer: I don't own Supernatural.**

* * *

And so Dean and Castiel went for the coffee date, which then turned into a lunch date, followed by an afternoon walk in the park date and on to a dinner date. They talked and laughed and kissed and held hands, and generally just enjoyed the knowledge that they were with the one they cared about and who cared about them in return. And so that was the start of the beautiful relationship of Castiel and Dean.

After that it was a common sight to see them together. Gabriel liked to claim it was all his doing, but those in the know ignored his comments. Dean and Castiel finally met Gabriel girlfriend who they both decided was a little bit scary and definitely not someone to mess with. Dean then introduced Castiel to Jess, Sam's fiancée, and that seemed to go better. Jess was lovely after all.

Sam was happy that his brother had found someone to be with. And Gabriel? Well he was ecstatic that Cassie had finally found someone to keep him grounded.

He was also glad that being with Dean seemed to smooth out some of Castiel's rough edges and he even started being slightly more polite to there clients. Not completely, but it was better than he had been before.

* * *

Then came the wedding of Sam and Jess, the one in Hawaii which had started it all. The one which required Dean to get into a plane.

While his fear seemed to have gone, or at least lessened when Castiel was in the pilots seat, the idea of getting into a plane being flown by someone else still horrified Dean. As such Castiel 'borrowed' (he so wasn't going to ever pay it back) some money from Gabriel and hired a plane that would carry the wedding party out to island. As such he flew them all out there, and while Dean was supposed to be sitting in the back with his brother, that didn't work for him, instead he took shotgun to Castiel and watched him work. Flying a machine that was so much more complicated than his angel's angel. And yet Cas made it look easy. Dean couldn't quite believe that Cas would do that for him. His boyfriend really was the most amazing man ever.

And Castiel sat there and allowed Dean to stare at him in that distracting way, knowing that once he had landed and they got to the hotel he was going to make the other man pay, with kisses and other things. Yes he was happy with Dean, in his relationship with Dean. Having Dean at his side felt right in all things in his mind.

And later once the ceremony had been and gone and Jess had become Mrs Samuel Winchester, the speeches had been given, Dean embarrassing his little brother with stories of his childhood as was the job of the best man, and the first dance danced, Dean and Castiel slipped away from the celebrations to walk along the beach hand in hand, in the moonlight. Both marveling at their luck at having such a man as the one beside them in their life. And Dean knew, the time was right to say what had been burning his tongue for a while.

"Cas, I love you." He whispered pulling his boyfriend to a standstill and turning to face him.

Castiel, hearing the words smiled. He had known for a while that they were true but this was the first time Dean had spoken them. Now all that was left was for him to return the sentiment.

"I love you too Dean. More than anything." He whispered against Dean's lips as he leaned forwards to kiss him but Dean raised his finger and put it over Castiel's lips making him frown.

"Even more than angel?" Dean asked mock seriously making Castiel throw back his head and laugh before he answered.

"Maybe not more, but definitely the same amount." With that Castiel pulled Dean to him and kissed him with all the passion he held for his man. The kiss continued as they slowly sank down onto the sand, arms and legs entangled with each other. If someone had been watching they would not have been able to see where one man finished and the other began, and Dean and Castiel felt that was a highly accurate description of there relationship. They weren't two individual men any more, but a couple, a unit. They completed each other, made each other better, and brought out the best of themselves. They were without a doubt perfect.

THE END

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 **So that's it my dears. I hope you liked this story, and thank you again to all of you who have favoured, followed and reviewed.**

 **Anyway that's it from me, adios amigos.**


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